7-Chloro-1,8-naphthyridin-2-amine → HCID 13983407, compound

HRID 580488

Reaction equation

HRID 580488 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[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:4]3[N:3]=[CH:2][S:1][CH:5]=3)=[O:8])=[N:11]2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 851997-Chloro-1,8-naphthyridin-2-amineHCID 3042714-Thiazolecarboxylic acid

Product 1

HCID 13983407HCID 13983407, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure is similar to that described in Example 2, but starting with 4-thiazolecarboxylic acid (4.8 g), N,N'-carbonyldiimidazole (7.5 g) and 2-amino-7-chloro-1,8-naphthyridine (4.8 g). The product obtained by precipitation in water is purified by recrystallization in dimethylformamide (350 cc). N-(7-Chloro-1,8-naphthyridin-2-yl)-4-thiazolecarboxamide (6 g), m.p. 325° C., is thereby obtained.

Workup

  1. customis purified by recrystallization in dimethylformamide (350 cc)

Sources & evidence

ORD record
ord-f0e5d4ae00d04eab8b097595cd343e10
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Linked notes

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