7-Chloro-1,8-naphthyridin-2-amine → HCID 13983409, compound

HRID 580490Notes

Reaction equation

HRID 580490 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[N:14][C:15]([Cl:21])=[CH:16][CH:17]=2)[N:12]=1>O>[Cl:21][C:15]1[N:14]=[C:13]2[C:18]([CH:19]=[CH:20][C:11]([NH:10][C:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:9])=[N:12]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 851997-Chloro-1,8-naphthyridin-2-amineHCID 950485-Chloro-2-thiophenecarboxylic acid

Product 1

HCID 13983409HCID 13983409, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure is similar to that described in Example 2, but starting with 5-chloro-2-thiophenecarboxylic acid (9.5 g), N,N'-carbonyldiimidazole (9.5 g) and 2-amino-7-chloro-1,8-naphthyridine (8 g). The product obtained by precipitation in water is purified by recrystallization in propanol (700 cc). N-(7-Chloro-1,8-naphthyridin-2-yl)-5-chloro-2-thiophenecarboxamide (8.3 g), m.p. 275° C., is thereby obtained.

Workup

  1. customis purified by recrystallization in propanol (700 cc)

Sources & evidence

ORD record
ord-db660284ac2b4ac3afb07fe65b632893
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Reaction notes

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