Acetonitrile → N-(7-Phenoxy-1,8-naphthyridin-2-yl)-3-dimethylaminobenzamide

HRID 235847

Reaction equation

[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.[NH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[N:17][C:18]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:19][CH:20]=2)[N:15]=1.C(#N)C>O>[O:24]([C:18]1[N:17]=[C:16]2[C:21]([CH:22]=[CH:23][C:14]([NH:13][C:6](=[O:8])[C:5]3[CH:9]=[CH:10][CH:11]=[C:3]([N:2]([CH3:1])[CH3:12])[CH:4]=3)=[N:15]2)=[CH:20][CH:19]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with 3-dimethylaminobenzoic acid (23.1 g), N,N'-carbonyldiimidazole (22.7 g) and 2-amino-7-phenoxy-1,8-naphthyridine (23.7 g). The product produced by precipitation in water (44 g; m.p. approximately 90° C.) is dissolved in boiling acetonitrile (1000 cc). After 3 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with acetonitrile (3×50 cc) and dried at 40° C. under reduced pressure (0.067 kPa). N-(7-Phenoxy-1,8-naphthyridin-2-yl)-3-dimethylaminobenzamide (32 g) is produced (m.p. 120° C.).

Workup

dissolutionis dissolved
customthe crystallised solid is separated by filtration
washwashed with acetonitrile (3×50 cc)
customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record: ord-10fe8bff54bd4a9784448665a62cc5e4
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04642308

Linked notes

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