DD261153A1

DD261153A1 - PROCESS FOR THE PREPARATION OF NEW 2-HETEROARYL-5-ACYLAMINO-THIAZOLENE

Info

Publication number: DD261153A1
Application number: DD30092687A
Authority: DD
Inventors: Hans W Modrow; Wilfried Thiel; Roland Mayer
Original assignee: Bitterfeld Chemie
Priority date: 1987-03-19
Filing date: 1987-03-19
Publication date: 1988-10-19

Abstract

Die Erfindung betrifft ein Verfahren zur Herstellung von neuen 2-Heteroaryl-5-acylaminothiazolen, die als optische Aufheller, und Pharmaka interessant sind. Das Ziel der Erfindung, bisher unbekannte 2-Heteroaryl-5-acylaminothiazole der Formel II, in der R Heteroaryl bedeutet, in hoher Ausbeute und Reinheit herzustellen, wurde dadurch geloest, dass Heteroaryl-5-aminothiazole der Formel I in geloester Form mit einem Acylierungsmittel umgesetzt werden. Als Acylierungsmittel eignen sich besonders die Saeureanhydride und Saeurechloride, wobei im letzten Fall eine Hilfsbase zugesetzt wird. Als Loesungsmittel fungieren die den Acylierungsmitteln zugrunde liegenden Saeuren, ueberschuessige Acylierungsmittel selbst sowie aprotische Loesungsmittel, vorzugsweise Acetonitril. Formel IIThe invention relates to a process for the preparation of novel 2-heteroaryl-5-acylaminothiazolen, which are interesting as optical brighteners, and pharmaceuticals. The aim of the invention, hitherto unknown 2-heteroaryl-5-acylaminothiazole of the formula II in which R is heteroaryl to produce in high yield and purity, was solved by heteroaryl-5-aminothiazole of formula I in geloester form with an acylating agent be implemented. Particularly suitable acylating agents are the acid anhydrides and acid chlorides, in which case an auxiliary base is added. The solvents used are the acids underlying the acylating agents, excess acylating agents themselves and aprotic solvents, preferably acetonitrile. Formula II

Description

embodiments

Allgemeine Vorschriften:General regulations:

Variante A 5 mmol Aminothiazol werden in einer minimalen Menge Säure, mit der acyliert werden soll (A-i), oder Acetonitril (A₂) in der Hitze gelöst, mit5-7,5mmol Säureanhydrid versetzt und 10 min weiter erhitzt. Die Acylderivatefaiien in der Regel schon in der Hitze aus, können aber auch mit Wasser gefällt werden. Sie werden abgesaugt, mit Wasser gewaschen und gegebenenfalls umkristallisiert.Variant A 5 mmol of aminothiazole are dissolved in a minimum amount of acid to be acylated (Ai) or acetonitrile (A ₂ ) in the heat, admixed with 5-7.5 mmol of acid anhydride and further heated for 10 minutes. The Acylderivatefaiienen usually already in the heat, but can also be precipitated with water. They are filtered off, washed with water and optionally recrystallized.

Variante B Man löst 5 mmol Aminothiazol in wenig heißem Acetonitril, setzt 5 mmol Pyridinzu, versetzt mit 5-6 mmol Säurechlorid und erhitzt kurz. Man verfährt dann weiter nach Variante A Die Acylverbindungen werden nach beiden Varianten in Ausbeuten >90% erhalten. Beispiele sind in der folgenden Tabelle enthalten.Variant B Dissolve 5 mmol of aminothiazole in a little hot acetonitrile, add 5 mmol of pyridine, add 5-6 mmol of acid chloride and heat briefly. The procedure is then continued according to variant A. The acyl compounds are obtained in both variants in yields> 90%. Examples are included in the following table.

Tabelle: 2-Heteroaryl-5-acylaminothiazoleder'FormelTable: 2-Heteroaryl-5-acylaminothiazole Der'Formel RR ππ IlIl Vai teVai te HH Scamp/Scamp / axisaxis Bei-examples Acylacyl -- 318-32318-32 C / T',"¹ VT.-, υ / jjiaj.¹ C / T ', " ¹ VT.-, υ / jjiaj. ¹ 11 -COCH₃ -COCH ₃

-GOCF-GOCF

-CJOC ^H₁--CJOC ^ H ₁ -

^Ä1 ^Ä 1

H3--145H3--145

316-319 / Chlorbenzen316-319 / chlorobenzene

J>J>

A.A.

314-317 / DM?314-317 / DM?

-'. ρTj- '. ρTj

oW.i.oW.i.

307-309307-309

-COCH-COCH

255-257 / DMP255-257 / DMP

Claims

Claim:

Process for the production of new ones

2-heteroaryl-5-acylaminothiazoles of the formula

• s-

(II)

in which R = heteroaryl, characterized in that 2-heteroaryl-5-aminothiazoles of the formula

(D,

in which R has the abovementioned meaning, is reacted with an acylating agent in a solvent.

Field of application of the invention

The invention relates to a process for the preparation of novel 2-heteroaryl-5-acylaminothiazolen which can be used as pharmaceuticals.

Characteristic of the known state of the art

So far, only a few 2-substituted-5-aminothiazoles or their acyl derivatives are known. 2-heteroaryl-5-acylaminothiazoles are still unknown.

Object of the invention

The aim of the invention is to develop hitherto unknown 2-heteroaryl-5-acylaminothiazole.

Explanation of the essence of the invention

The object of the invention is to produce new 2-heteroaryl-5-acylaminothiazole in a simple manner in high yield and purity.

According to the invention the object is achieved in that 2-heteroaryl-5-aminothiazole of the formula

R - <

^ H

in which R = heteroaryl, be reacted in dissolved form with an Acylierungsmittei and thereby previously unknown 2-heteroaryl-5-acylaminothiazole of the formula

NH acyl

S-ir

in which R has the abovementioned meaning, arise in high purity.

Particularly suitable acylating agents are the acid anhydrides and acid chlorides, in which case an auxiliary base must be added. Suitable solvents are the acids on which the acylating agents are based, excess acylating agents and aprotic solvents, preferably acetonitrile.