CN106632303A - Preparation method of 6-thiazolylindole derivative - Google Patents
Preparation method of 6-thiazolylindole derivative Download PDFInfo
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- CN106632303A CN106632303A CN201710014283.9A CN201710014283A CN106632303A CN 106632303 A CN106632303 A CN 106632303A CN 201710014283 A CN201710014283 A CN 201710014283A CN 106632303 A CN106632303 A CN 106632303A
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- JEWQKBKNWNWXQZ-UHFFFAOYSA-N 2-(1H-indol-6-yl)-1,3-thiazole Chemical class N1C=CC2=CC=C(C=C12)C=1SC=CN=1 JEWQKBKNWNWXQZ-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims abstract description 12
- 238000006722 reduction reaction Methods 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 11
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 238000011938 amidation process Methods 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 9
- KWBIXTIBYFUAGV-UHFFFAOYSA-N ethylcarbamic acid Chemical compound CCNC(O)=O KWBIXTIBYFUAGV-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 229940125782 compound 2 Drugs 0.000 claims description 7
- 229940126214 compound 3 Drugs 0.000 claims description 7
- 229940125898 compound 5 Drugs 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 230000000977 initiatory effect Effects 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 8
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 4
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 claims 4
- 229940113088 dimethylacetamide Drugs 0.000 claims 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 2
- 239000012448 Lithium borohydride Substances 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910000085 borane Inorganic materials 0.000 claims 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 1
- 235000005074 zinc chloride Nutrition 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 230000009435 amidation Effects 0.000 abstract 1
- 238000007112 amidation reaction Methods 0.000 abstract 1
- 239000012450 pharmaceutical intermediate Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical class CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- DZAHXNNEQCZPGJ-UHFFFAOYSA-N CCCCOC(OC)=O.COC(O)=O Chemical compound CCCCOC(OC)=O.COC(O)=O DZAHXNNEQCZPGJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention discloses a preparation method of a 6-thiazolylindole derivative of tert-butyl 2-(6-thiazolyl-1H-indol-3-yl) ethylcarbamic acid. 6-thiazolylindole is used as a starting raw material and friedel-crafts reaction, amidation, reduction and t-butyloxycarboryl protection reaction are conducted to get the target products. The compound is an important pharmaceutical intermediate.
Description
Technical field
The present invention relates to a kind of novel processing step of medicine intermediate, more particularly to a kind of 6- thiazolyls indole derivatives
The preparation method of tert-butyl group 2- (6- thiazolyl -1H- indol-3-yls) ethyl carbamic acid.
Technical background
Compound tert-butyl group 2- (6- thiazolyl -1H- indol-3-yls) ethyl carbamic acid, structural formula is：
The derivative of this compound tert-butyl group 2- (6- thiazolyl -1H- indol-3-yls) ethyl carbamic acids and correlation is in medicine
Have in thing chemistry and organic synthesis and be widely used.Current tert-butyl group 2- (6- thiazolyl -1H- indol-3-yls) ethylamino first
The synthesis of acid is more difficult.Accordingly, it would be desirable to develop a raw material be easy to get, it is easy to operate, react easily controllable, overall yield is suitable
Synthetic method.
The content of the invention
The invention discloses one kind prepares the side of tert-butyl group 2- (6- thiazolyl -1H- indol-3-yls) ethyl carbamic acid
Method, with 6- thiazolyl indoles as initiation material, through Friedel-Crafts reaction, amidatioon, reduction, tertbutyloxycarbonyl protection reaction mesh is obtained
Mark product 5, synthesis step is as follows：
(1) with 6- thiazolyl indoles as initiation material, 2 are obtained through Friedel-Crafts reaction；
(2) amidation process is carried out 2, obtains 3；
(3) carry out reduction reaction 3 and obtain 4；
(4) carry out tertbutyloxycarbonyl protection reaction 4 and obtain 5；
One preferred embodiment in, the lewis acid used by described Friedel-Crafts reaction prepare compound 2 be selected from trichlorine
Change aluminium；Reagent used by described amidation process prepare compound 3 is selected from ammoniacal liquor；Described reduction reaction prepare compound 4
Reducing agent used is selected from lithium aluminium hydride；Reagent used by described tertbutyloxycarbonyl protection reaction prepare compound 5 is selected from two
Dimethyl dicarbonate butyl ester.
One preferred embodiment in, the solvent used by described Friedel-Crafts reaction prepare compound 2 be selected from dichloromethane；
Solvent used by described amidation process prepare compound 3 is selected from water；It is molten used by described reduction reaction prepare compound 4
Agent is selected from tetrahydrofuran；Solvent used by described tertbutyloxycarbonyl protection reaction prepare compound 5 is selected from dichloromethane.
One preferred embodiment in, the reaction temperature used by described Friedel-Crafts reaction prepare compound 2 is solvent
Reflux temperature；Temperature used by described amidation process prepare compound 3 is the room temperature of solvent；It is prepared by described reduction reaction
Temperature used by compound 4 is the reflux temperature of solvent；Temperature used by described tertbutyloxycarbonyl protection reaction prepare compound 5
Degree is room temperature.
The present invention relates to a kind of preparation method of tert-butyl group 2- (6- thiazolyl -1H- indol-3-yls) ethyl carbamic acid,
Currently without other Patents documents reports.
The present invention is further described by the following embodiment, and these descriptions are not present invention to be made into one
The restriction of step.It should be understood by those skilled in the art that the equivalent that the technical characteristic of the present invention is made, or change accordingly
Enter, still fall within protection scope of the present invention.
Specific embodiment mode
Embodiment 1
(1) synthesis of 2- (6- thiazolyl -1H- indol-3-yls) -2- oxo chloroacetic chlorides
40g 6- thiazolyl indoles is added in 450ml anhydrous methylene chlorides, 15g alchlors are added, 60g is added
Oxalyl chloride, is heated to reflux 2 hours, is cooled to room temperature, adds water, point liquid, drying, concentration, the isolated 47g of residue upper prop
2- (6- thiazolyl -1H- indol-3-yls) -2- oxo chloroacetic chlorides.
(2) synthesis of 2- (6- thiazolyl -1H- indol-3-yls) -2- oxoaGetamides
45g2- (6- thiazolyl -1H- indol-3-yls) -2- oxo chloroacetic chlorides are added to 100ml water with 500ml ammoniacal liquor
In mixture, it is stirred at room temperature 4 hours, adds ethyl acetate extraction, divide liquid, drying, concentration, silica gel post separation is obtained on residue
32g 2- (6- thiazolyl -1H- indol-3-yls) -2- oxoaGetamides.
(3) synthesis of 2- (6- thiazolyl -1H- indol-3-yls) ethamine
30g 2- (6- thiazolyl -1H- indol-3-yls) -2- oxoaGetamides are added to 200ml anhydrous tetrahydro furans
In, 16g Lithium Aluminium Hydrides are added, stirring 8 hours is heated to reflux, room temperature is cooled to, sodium hydrate aqueous solution is added, add acetic acid second
Ester is extracted, and is dried, is concentrated, and silica gel post separation obtains 16g 2- (6- thiazolyl -1H- indol-3-yls) ethamine on residue.
(4) synthesis of tert-butyl group 2- (6- thiazolyl -1H- indol-3-yls) ethyl carbamic acid
15g 2- (6- thiazolyl -1H- indol-3-yls) ethamine is added in 150ml dichloromethane, the carbon of 18g bis- is added
Sour di tert butyl carbonate, adds 0.5g 4- dimethylamino pyridines, is stirred at room temperature 10 hours, and concentration removes dichloromethane, on residue
Silica gel post separation obtains 12g tert-butyl group 2- (6- thiazolyl -1H- indol-3-yls) ethyl carbamic acid.
Claims (6)
1. one kind prepares 6- thiazolyl indole derivatives tert-butyl group 2- (6- thiazolyl -1H- indol-3-yls) ethyl carbamic acid
Preparation method, with 6- thiazolyl indoles as initiation material, through Friedel-Crafts reaction, amidatioon, reduction, tertbutyloxycarbonyl protection reaction
Target product 5 is obtained, synthetic route is as follows,
2. method according to claim 1, it is characterized by described 4 steps reaction is,
(1) with 6- thiazolyl indoles as initiation material, 2 are obtained through Friedel-Crafts reaction；
(2) amidation process is carried out 2, obtains 3；
(3) carry out reduction reaction 3 and obtain 4；
(4) carry out tertbutyloxycarbonyl protection reaction 4 and obtain 5；
3. method according to claim 1, it is characterised in that the lewis acid used by described Friedel-Crafts reaction prepare compound 2
The mixture of one or more in alchlor, ferric trichloride, zinc chloride, stannic chloride；Described amidation process system
One or two mixture of the reagent used by standby compound 3 in ammonia, ammoniacal liquor；Described reduction reaction prepares chemical combination
Reducing agent used by thing 4 is in sodium borohydride, potassium borohydride, lithium borohydride, sodium cyanoborohydride, lithium aluminium hydride, borine
The mixture of one or more；Reagent used by described tertbutyloxycarbonyl protection reaction prepare compound 5 is selected from two carbonic acid two
The tert-butyl ester.
4. method according to claim 1, it is characterised in that the solvent used by described Friedel-Crafts reaction prepare compound 2 is selected from
Methyl alcohol, ethanol, normal propyl alcohol, isopropanol, tetrahydrofuran, dichloromethane, toluene, ortho-xylene, paraxylene, meta-xylene, N,
The mixture of one or more in dinethylformamide, DMAC N,N' dimethyl acetamide；Described amidation process preparationization
It is solvent selected from methanol, ethanol, normal propyl alcohol, isopropanol, tetrahydrofuran, dichloromethane, toluene, ortho-xylene used by compound 3, right
The mixture of one or more in dimethylbenzene, meta-xylene, N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, water；Institute
Solvent selected from methanol, ethanol, normal propyl alcohol, isopropanol, tetrahydrofuran, the dichloromethane used by reduction reaction prepare compound 4 stated
Alkane, toluene, ortho-xylene, paraxylene, meta-xylene, N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, trichlorine oxygen
The mixture of one or more in phosphorus, thionyl chloride；It is molten used by described tertbutyloxycarbonyl protection reaction prepare compound 5
Agent is selected from methyl alcohol, ethanol, normal propyl alcohol, isopropanol, tetrahydrofuran, dichloromethane, toluene, ortho-xylene, paraxylene, a diformazan
The mixture of one or more in benzene, N,N-dimethylformamide, DMAC N,N' dimethyl acetamide.
5. method according to claim 1, it is characterised in that the reaction temperature used by described Friedel-Crafts reaction prepare compound 2
It is the reflux temperature of 0 DEG C～solvent；Temperature used by described amidation process prepare compound 3 is the backflow of 0 DEG C～solvent
Temperature；Temperature used by described reduction reaction prepare compound 4 is the reflux temperature of 0 DEG C～solvent；Described tertiary butyloxycarbonyl
Temperature used by base protection reaction prepare compound 5 is the reflux temperature of 0 DEG C～solvent.
6. method according to claim 1, it is characterised in that the reaction temperature used by described Friedel-Crafts reaction prepare compound 2
It is the reflux temperature of solvent；Temperature used by described amidation process prepare compound 3 is the room temperature of solvent；Described reduction
Temperature used by reaction prepare compound 4 is the reflux temperature of solvent；Described tertbutyloxycarbonyl protection reaction prepare compound 5
Temperature used is room temperature.
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| CN201710014283.9A CN106632303A (en) | 2017-01-09 | 2017-01-09 | Preparation method of 6-thiazolylindole derivative |
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| CN201710014283.9A CN106632303A (en) | 2017-01-09 | 2017-01-09 | Preparation method of 6-thiazolylindole derivative |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025147509A1 (en) * | 2024-01-03 | 2025-07-10 | Kymera Therapeutics, Inc. | Stat6 inhibitors and uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1610547A (en) * | 2001-03-29 | 2005-04-27 | 伊莱利利公司 | N-(2-arylethyl)benzylamines as antagonists of the 5-HT6 receptor |
| CN102307868A (en) * | 2009-02-04 | 2012-01-04 | 詹森药业有限公司 | Indole derivatives as anticancer agents |
| CN103923135A (en) * | 2014-04-28 | 2014-07-16 | 南京靖龙药物研发有限公司 | Deuterated 5-hydroxy tryptophan glucoside derivatives and preparation method thereof |
| CN104292145A (en) * | 2014-10-12 | 2015-01-21 | 湖南华腾制药有限公司 | Preparation method of 6-bromoindole derivative |
-
2017
- 2017-01-09 CN CN201710014283.9A patent/CN106632303A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1610547A (en) * | 2001-03-29 | 2005-04-27 | 伊莱利利公司 | N-(2-arylethyl)benzylamines as antagonists of the 5-HT6 receptor |
| CN102307868A (en) * | 2009-02-04 | 2012-01-04 | 詹森药业有限公司 | Indole derivatives as anticancer agents |
| CN103923135A (en) * | 2014-04-28 | 2014-07-16 | 南京靖龙药物研发有限公司 | Deuterated 5-hydroxy tryptophan glucoside derivatives and preparation method thereof |
| CN104292145A (en) * | 2014-10-12 | 2015-01-21 | 湖南华腾制药有限公司 | Preparation method of 6-bromoindole derivative |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025147509A1 (en) * | 2024-01-03 | 2025-07-10 | Kymera Therapeutics, Inc. | Stat6 inhibitors and uses thereof |
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Application publication date: 20170510 |