6-Methoxypyridazine-3-carboxylic acid → N-(7-Phenoxy-1,8-naphthyridin-2-yl)-6-methoxy-3-pyridazinecarboxamide

HRID 580498Notes

Reaction equation

HRID 580498 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[N:7][C:6]([C:9]([OH:11])=O)=[CH:5][CH:4]=1.[NH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[N:16][C:17]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:18][CH:19]=2)[N:14]=1>O>[O:23]([C:17]1[N:16]=[C:15]2[C:20]([CH:21]=[CH:22][C:13]([NH:12][C:9]([C:6]3[N:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[O:11])=[N:14]2)=[CH:19][CH:18]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 122144616-Methoxypyridazine-3-carboxylic acidHCID 137873732-Amino-7-phenoxy-1,8-naphthyridine

Product 1

HCID 13983417N-(7-Phenoxy-1,8-naphthyridin-2-yl)-6-methoxy-3-pyridazinecarboxamideYield 70.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure is similar to that described in Example 2, but starting with 6-methoxy-3-pyridazinecarboxylic acid (2.2 g), N,N'-carbonyldiimidazole (2.3 g) and 2-amino-7-phenoxy-1,8-naphthyridine (2.7 g). The product obtained by precipitation in water is purified by recrystallization in acetonitrile (300 cc). N-(7-Phenoxy-1,8-naphthyridin-2-yl)-6-methoxy-3-pyridazinecarboxamide (3 g), m.p. 95° C., is thereby obtained.

Workup

  1. customis purified by recrystallization in acetonitrile (300 cc)

Sources & evidence

ORD record
ord-a49274d826ea4ac192ea7c092976a639
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Reaction notes

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