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

HRID 235856Notes

Reaction equation

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

Participants

Conditions

Temperature: 4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with 3-thiophenecarboxylic acid (5 g), N,N'-carbonyldiimidazole (6.3 g) and 2-amino-7-phenoxy-1,8-naphthyridine (8.3 g). The product produced by precipitation in water (11.6 g; m.p. 110° C.) is dissolved in boiling acetonitrile (50 cc). After 2 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with diisopropyl ether (3×10 cc) and dried at 35° C. under reduced pressure (0.067 kPa). N-(7-Phenoxy-1,8-naphthyridin-2-yl)-3-thiophenecarboxamide (8.2 g) is produced, m.p. 95° C.

Workup

dissolutionis dissolved
customthe crystallised solid is separated by filtration
washwashed with diisopropyl ether (3×10 cc)
customdried at 35° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record: ord-9a20e9badb704887b311b009ef850f10
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04642308

Reaction notes

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