7-Chloro-1,8-naphthyridin-2-amine → HCID 13983410, compound

HRID 580491Notes

Reaction equation

HRID 580491 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]([OH:10])=O)=[CH:5][CH:4]=1.[NH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[N:13]=1>O>[Cl:22][C:16]1[N:15]=[C:14]2[C:19]([CH:20]=[CH:21][C:12]([NH:11][C:8]([C:6]3[S:7][C:3]([S:2][CH3:1])=[CH:4][CH:5]=3)=[O:10])=[N:13]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 851997-Chloro-1,8-naphthyridin-2-amineHCID 7143725-(Methylsulfanyl)thiophene-2-carboxylic acid

Product 1

HCID 13983410HCID 13983410, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure is similar to that described in Example 2, but starting with 5-methylthio-2-thiophenecarboxylic acid (5.6 g), N,N'-carbonyldiimidazole (5.2 g) and 2-amino-7-chloro-1,8-naphthyridine (4.3 g). The product obtained by precipitation in water is purified by recrystallization in a dimethylformamide/methanol (5:5 by volume) mixture (200 cc). N-(7-Chloro-1,8-naphthyridin-2-yl)-5-methylthio-2-thiophenecarboxamide (6.1 g), m.p. 235° C., is thereby obtained.

Workup

  1. customis purified by recrystallization in a dimethylformamide/methanol (5:5 by volume) mixture (200 cc)

Sources & evidence

ORD record
ord-fd455909f4524232bef5786761e2f1e1
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Reaction notes

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