CA2394891A1 - Substituted phthalocyanines and their precursors - Google Patents

Info

Publication number

CA2394891A1

CA2394891A1 CA002394891A CA2394891A CA2394891A1 CA 2394891 A1 CA2394891 A1 CA 2394891A1 CA 002394891 A CA002394891 A CA 002394891A CA 2394891 A CA2394891 A CA 2394891A CA 2394891 A1 CA2394891 A1 CA 2394891A1

Authority

CA

Canada

Prior art keywords

substituted

optionally substituted

formula

alkyl

different

Prior art date

1999-12-08

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000002243 precursor Substances 0.000 title description 7
• 229920006391 phthalonitrile polymer Polymers 0.000 claims abstract description 176
• 238000000034 method Methods 0.000 claims abstract description 157
• -1 phthalonitrile sulfonate esters Chemical class 0.000 claims abstract description 123
• 238000002360 preparation method Methods 0.000 claims abstract description 119
• 230000008569 process Effects 0.000 claims abstract description 81
• IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 186
• 125000001246 bromo group Chemical group Br* 0.000 claims description 156
• XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 claims description 155
• 238000006243 chemical reaction Methods 0.000 claims description 149
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 136
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 92
• 125000000217 alkyl group Chemical group 0.000 claims description 78
• 125000001424 substituent group Chemical group 0.000 claims description 70
• 239000000203 mixture Substances 0.000 claims description 68
• 125000003342 alkenyl group Chemical group 0.000 claims description 61
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 51
• 229910052763 palladium Inorganic materials 0.000 claims description 51
• 125000003118 aryl group Chemical group 0.000 claims description 50
• 239000007787 solid Substances 0.000 claims description 48
• 150000001875 compounds Chemical class 0.000 claims description 47
• PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 47
• 229910052725 zinc Inorganic materials 0.000 claims description 43
• 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 40
• 238000006880 cross-coupling reaction Methods 0.000 claims description 37
• 239000003153 chemical reaction reagent Substances 0.000 claims description 35
• 229920000642 polymer Polymers 0.000 claims description 35
• 229920006395 saturated elastomer Polymers 0.000 claims description 34
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 150000004820 halides Chemical class 0.000 claims description 24
• 230000002093 peripheral effect Effects 0.000 claims description 24
• 125000000304 alkynyl group Chemical group 0.000 claims description 23
• 239000000463 material Substances 0.000 claims description 23
• 229920001184 polypeptide Polymers 0.000 claims description 22
• 102000004196 processed proteins & peptides Human genes 0.000 claims description 22
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 22
• 150000001413 amino acids Chemical class 0.000 claims description 21
• 229910052759 nickel Inorganic materials 0.000 claims description 21
• 206010028980 Neoplasm Diseases 0.000 claims description 20
• 229910052751 metal Inorganic materials 0.000 claims description 20
• 239000002184 metal Substances 0.000 claims description 20
• 102000004169 proteins and genes Human genes 0.000 claims description 20
• 108090000623 proteins and genes Proteins 0.000 claims description 20
• 150000001720 carbohydrates Chemical class 0.000 claims description 19
• 235000014113 dietary fatty acids Nutrition 0.000 claims description 19
• 239000000194 fatty acid Substances 0.000 claims description 19
• 229930195729 fatty acid Natural products 0.000 claims description 19
• 150000004665 fatty acids Chemical class 0.000 claims description 19
• 150000004676 glycans Chemical class 0.000 claims description 19
• 150000007523 nucleic acids Chemical class 0.000 claims description 19
• 102000039446 nucleic acids Human genes 0.000 claims description 19
• 108020004707 nucleic acids Proteins 0.000 claims description 19
• 229920001282 polysaccharide Polymers 0.000 claims description 19
• 239000005017 polysaccharide Substances 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 229910052749 magnesium Inorganic materials 0.000 claims description 16
• 238000002428 photodynamic therapy Methods 0.000 claims description 16
• MPAIWVOBMLSHQA-UHFFFAOYSA-N 3,6-dihydroxybenzene-1,2-dicarbonitrile Chemical class OC1=CC=C(O)C(C#N)=C1C#N MPAIWVOBMLSHQA-UHFFFAOYSA-N 0.000 claims description 15
• 229910052697 platinum Inorganic materials 0.000 claims description 15
• 229910052710 silicon Inorganic materials 0.000 claims description 15
• 229910052782 aluminium Inorganic materials 0.000 claims description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 13
• 238000005859 coupling reaction Methods 0.000 claims description 13
• 150000002148 esters Chemical class 0.000 claims description 13
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• 239000001257 hydrogen Substances 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 230000005855 radiation Effects 0.000 claims description 12
• 239000000126 substance Substances 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 230000008878 coupling Effects 0.000 claims description 11
• 238000010168 coupling process Methods 0.000 claims description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
• 208000031295 Animal disease Diseases 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 201000010099 disease Diseases 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 206010020718 hyperplasia Diseases 0.000 claims description 10
• 229910052740 iodine Inorganic materials 0.000 claims description 10
• 239000007819 coupling partner Substances 0.000 claims description 9
• 230000005670 electromagnetic radiation Effects 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 8
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 8
• 150000002367 halogens Chemical group 0.000 claims description 8
• 230000003647 oxidation Effects 0.000 claims description 8
• 238000007254 oxidation reaction Methods 0.000 claims description 8
• 230000001413 cellular effect Effects 0.000 claims description 7
• 230000005292 diamagnetic effect Effects 0.000 claims description 7
• 229910052732 germanium Inorganic materials 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 229910052738 indium Inorganic materials 0.000 claims description 7
• 229910001509 metal bromide Inorganic materials 0.000 claims description 7
• 229910001510 metal chloride Inorganic materials 0.000 claims description 7
• 229910044991 metal oxide Inorganic materials 0.000 claims description 7
• 150000004706 metal oxides Chemical class 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• 230000003287 optical effect Effects 0.000 claims description 7
• 239000010703 silicon Substances 0.000 claims description 7
• 201000004681 Psoriasis Diseases 0.000 claims description 6
• 229910052791 calcium Inorganic materials 0.000 claims description 6
• 229910052802 copper Inorganic materials 0.000 claims description 6
• 229910052733 gallium Inorganic materials 0.000 claims description 6
• 229910052742 iron Inorganic materials 0.000 claims description 6
• 229910052747 lanthanoid Inorganic materials 0.000 claims description 6
• 150000002602 lanthanoids Chemical class 0.000 claims description 6
• 229910052745 lead Inorganic materials 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 229910052758 niobium Inorganic materials 0.000 claims description 6
• 229910052718 tin Inorganic materials 0.000 claims description 6
• 229910052720 vanadium Inorganic materials 0.000 claims description 6
• 208000015602 Actinic lichen planus Diseases 0.000 claims description 5
• 208000037260 Atherosclerotic Plaque Diseases 0.000 claims description 5
• 208000035143 Bacterial infection Diseases 0.000 claims description 5
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 5
• 201000004624 Dermatitis Diseases 0.000 claims description 5
• 208000031220 Hemophilia Diseases 0.000 claims description 5
• 208000009292 Hemophilia A Diseases 0.000 claims description 5
• 208000031888 Mycoses Diseases 0.000 claims description 5
• 206010057469 Vascular stenosis Diseases 0.000 claims description 5
• 208000009621 actinic keratosis Diseases 0.000 claims description 5
• 230000002152 alkylating effect Effects 0.000 claims description 5
• 206010003246 arthritis Diseases 0.000 claims description 5
• 208000010668 atopic eczema Diseases 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 230000002538 fungal effect Effects 0.000 claims description 5
• 230000002757 inflammatory effect Effects 0.000 claims description 5
• 230000003211 malignant effect Effects 0.000 claims description 5
• 201000005962 mycosis fungoides Diseases 0.000 claims description 5
• 239000012038 nucleophile Substances 0.000 claims description 5
• 201000008482 osteoarthritis Diseases 0.000 claims description 5
• 208000037803 restenosis Diseases 0.000 claims description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
• 150000003839 salts Chemical class 0.000 claims description 5
• 230000002792 vascular Effects 0.000 claims description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• 230000003612 virological effect Effects 0.000 claims description 5
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 229920001577 copolymer Polymers 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 229920000728 polyester Polymers 0.000 claims description 4
• 229920001223 polyethylene glycol Polymers 0.000 claims description 4
• 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 4
• 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 4
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 4
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
• 206010029113 Neovascularisation Diseases 0.000 claims description 3
• 230000001427 coherent effect Effects 0.000 claims description 3
• 229910021419 crystalline silicon Inorganic materials 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 230000000704 physical effect Effects 0.000 claims description 3
• 238000007920 subcutaneous administration Methods 0.000 claims description 3
• 230000009885 systemic effect Effects 0.000 claims description 3
• 230000000699 topical effect Effects 0.000 claims description 3
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 3
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 2
• 229920002732 Polyanhydride Polymers 0.000 claims description 2
• 229920001710 Polyorthoester Polymers 0.000 claims description 2
• 229920002988 biodegradable polymer Polymers 0.000 claims description 2
• 239000004621 biodegradable polymer Substances 0.000 claims description 2
• 229920001400 block copolymer Polymers 0.000 claims description 2
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
• 238000005286 illumination Methods 0.000 claims description 2
• OKPYIWASQZGASP-UHFFFAOYSA-N n-(2-hydroxypropyl)-2-methylprop-2-enamide Chemical group CC(O)CNC(=O)C(C)=C OKPYIWASQZGASP-UHFFFAOYSA-N 0.000 claims description 2
• 229920001308 poly(aminoacid) Polymers 0.000 claims description 2
• 229920002627 poly(phosphazenes) Polymers 0.000 claims description 2
• 125000003107 substituted aryl group Chemical group 0.000 claims description 2
• 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 50
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 24
• 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims 21
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 15
• 229910006069 SO3H Inorganic materials 0.000 claims 12
• 125000006755 (C2-C20) alkyl group Chemical group 0.000 claims 1
• 229910052731 fluorine Inorganic materials 0.000 claims 1
• 102220009232 rs111430410 Human genes 0.000 claims 1
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 288
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 156
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 150
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 126
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 112
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 108
• 239000000243 solution Substances 0.000 description 102
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
• 239000003480 eluent Substances 0.000 description 78
• UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 73
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 72
• 239000002904 solvent Substances 0.000 description 71
• 238000010992 reflux Methods 0.000 description 70
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 68
• 238000005481 NMR spectroscopy Methods 0.000 description 66
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 63
• 239000011701 zinc Substances 0.000 description 63
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 60
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 58
• PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 54
• 238000004440 column chromatography Methods 0.000 description 53
• 239000000047 product Substances 0.000 description 53
• 239000000377 silicon dioxide Substances 0.000 description 51
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 49
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
• NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 45
• 101150041968 CDC13 gene Proteins 0.000 description 42
• DSZGQEHPKNNPFU-UHFFFAOYSA-N 3,6-didecylbenzene-1,2-dicarbonitrile Chemical compound CCCCCCCCCCC1=CC=C(CCCCCCCCCC)C(C#N)=C1C#N DSZGQEHPKNNPFU-UHFFFAOYSA-N 0.000 description 41
• 238000005160 1H NMR spectroscopy Methods 0.000 description 37
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• 210000004027 cell Anatomy 0.000 description 35
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 35
• 239000003208 petroleum Substances 0.000 description 35
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 32
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 31
• 235000019439 ethyl acetate Nutrition 0.000 description 31
• 239000012267 brine Substances 0.000 description 30
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 30
• 229910052757 nitrogen Inorganic materials 0.000 description 30
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
• 229910052786 argon Inorganic materials 0.000 description 29
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
• 229940093499 ethyl acetate Drugs 0.000 description 28
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
• 208000028257 Joubert syndrome with oculorenal defect Diseases 0.000 description 26
• 239000003054 catalyst Substances 0.000 description 26
• 238000001816 cooling Methods 0.000 description 26
• AYGKNJJGSMKDPA-UHFFFAOYSA-N 4-bromo-3,6-dibutoxybenzene-1,2-dicarbonitrile Chemical compound CCCCOC1=CC(Br)=C(OCCCC)C(C#N)=C1C#N AYGKNJJGSMKDPA-UHFFFAOYSA-N 0.000 description 25
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 25
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 21
• FCAPKPPCJBYHEC-UHFFFAOYSA-N [2,3-dicyano-4-(trifluoromethylsulfonyloxy)phenyl] trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=C(OS(=O)(=O)C(F)(F)F)C(C#N)=C1C#N FCAPKPPCJBYHEC-UHFFFAOYSA-N 0.000 description 20
• 239000003921 oil Substances 0.000 description 20
• 239000000523 sample Substances 0.000 description 20
• ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 19
• 230000015572 biosynthetic process Effects 0.000 description 19
• 238000003756 stirring Methods 0.000 description 19
• 239000004246 zinc acetate Substances 0.000 description 19
• 239000012043 crude product Substances 0.000 description 18
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 17
• 239000013078 crystal Substances 0.000 description 17
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• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 15
• 230000000155 isotopic effect Effects 0.000 description 14
• 238000001906 matrix-assisted laser desorption--ionisation mass spectrometry Methods 0.000 description 14
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
• LVIYYTJTOKJJOC-UHFFFAOYSA-N nickel phthalocyanine Chemical compound [Ni+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 LVIYYTJTOKJJOC-UHFFFAOYSA-N 0.000 description 13
• 238000003786 synthesis reaction Methods 0.000 description 13
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• HAAHMAILBWIUSO-UHFFFAOYSA-N 4,5-dibromo-3,6-dibutoxybenzene-1,2-dicarbonitrile Chemical compound CCCCOC1=C(Br)C(Br)=C(OCCCC)C(C#N)=C1C#N HAAHMAILBWIUSO-UHFFFAOYSA-N 0.000 description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• FDGUZCMQOHCDOY-UHFFFAOYSA-M [I-].CCCCCCCCCC[Zn+] Chemical compound [I-].CCCCCCCCCC[Zn+] FDGUZCMQOHCDOY-UHFFFAOYSA-M 0.000 description 12
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 12
• 229960004132 diethyl ether Drugs 0.000 description 12
• 239000011777 magnesium Substances 0.000 description 12
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
• 239000002274 desiccant Substances 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
• 239000011133 lead Substances 0.000 description 11
• CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 description 11
• 238000006862 quantum yield reaction Methods 0.000 description 11
• 229960000583 acetic acid Drugs 0.000 description 10
• 229910052744 lithium Inorganic materials 0.000 description 10
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 10
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