5-Bromo-2-furanecarboxylic acid → HCID 13983411, compound

HRID 580492Notes

Reaction equation

HRID 580492 reaction equation
[Br:1][C:2]1[O: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[O:6][C:2]([Br:1])=[CH:3][CH:4]=3)=[O:9])=[N:12]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 685115-Bromo-2-furanecarboxylic acidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13983411HCID 13983411, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure is similar to that described in Example 2, but starting with 5-bromo-2-furancarboxylic acid (2.9 g), N,N'-carbonyldiimidazole (2.4 g) and 2-amino-7-chloro-1,8-naphthyridine (1.8 g). The product obtained by precipitation in water is purified by recrystallization in a dimethylformamide/methanol (5:5 by volume) mixture (100 cc). N-(7-Chloro-1,8-naphthyridin-2-yl)-5-bromo-2-furancarboxamide (2.6 g), m.p. 285° C., is thereby obtained.

Workup

  1. customis purified by recrystallization in a dimethylformamide/methanol (5:5 by volume) mixture (100 cc)

Sources & evidence

ORD record
ord-1d5ea2015e6b446a8711108fef8e0378
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Reaction notes

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