Acetonitrile → N-(7-chloro-1,8-naphthyridin-2-yl)-3-fluorobenzamide

HRID 235812Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[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.C(#N)C>O>[Cl:22][C:16]1[N:15]=[C:14]2[C:19]([CH:20]=[CH:21][C:12]([NH:11][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)=[N:13]2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with 3-fluorobenzoic acid (20 g), N,N'-carbonyldiimidazole (23 g) and 2-amino-7-chloro-1,8-naphthyridine (16.9 g). The product produced by precipitation in water (25 g; m.p. 201° C.) is dissolved in boiling acetonitrile (230 cc). After 4 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with acetonitrile (2×20 cc) and dried at 40° C. under reduced pressure (0.067 kPa). N-(7-chloro-1,8-naphthyridin-2-yl)-3-fluorobenzamide (21.4 g) is produced, m.p. 202° C. EXAMPLE 15

Workup

dissolutionis dissolved
customthe crystallised solid is separated by filtration
washwashed with acetonitrile (2×20 cc)
customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record: ord-81906540c37c408e9a9cb258edbf692e
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04642308

Reaction notes

Loading…