Thiazole-5-carboxylic acid → N-(7-Chloro-1,8-naphthyridin-2-yl)-5-thiazolecarboxamide

HRID 580489

Reaction equation

HRID 580489 reaction equation
[S:1]1[C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=[CH:2]1.[NH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[N:13][C:14]([Cl:20])=[CH:15][CH:16]=2)[N:11]=1>O>[Cl:20][C:14]1[N:13]=[C:12]2[C:17]([CH:18]=[CH:19][C:10]([NH:9][C:6]([C:5]3[S:1][CH:2]=[N:3][CH:4]=3)=[O:8])=[N:11]2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 84494Thiazole-5-carboxylic acidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13983408N-(7-Chloro-1,8-naphthyridin-2-yl)-5-thiazolecarboxamideYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure is similar to that described in Example 2, but starting with 5-thiazolecarboxylic acid (4.5 g), N,N'-carbonyldiimidazole (6.8 g) and 2-amino-7-chloro-1,8-naphthyridine (5 g). The product obtained by precipitation in water is purified by recrystallization in a dimethylformamide/acetonitrile (5:5 by volume) mixture (120 cc). N-(7-Chloro-1,8-naphthyridin-2-yl)-5-thiazolecarboxamide (5.5 g), m.p. 292° C., is thereby obtained.

Workup

  1. customis purified by recrystallization in a dimethylformamide/acetonitrile (5:5 by volume) mixture (120 cc)

Sources & evidence

ORD record
ord-8f0a3522ed364424b0f2c82f36caa01d
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Linked notes

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