Ethanol → N-(7-phenoxy-1,8-naphthyridin-2-yl)cyclopropanecarboxamide

HRID 235803Notes

Reaction equation

[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.[NH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[N:11][C:12]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:14]=2)[N:9]=1.C(O)C>O>[O:18]([C:12]1[N:11]=[C:10]2[C:15]([CH:16]=[CH:17][C:8]([NH:7][C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:6])=[N:9]2)=[CH:14][CH:13]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with cyclopropanecarboxylic acid (4.8 g), N,N'-carbonyldiimidazole (9.07 g) and 2-amino-7-phenoxy-1,8-naphthyridine (10 g). The product produced by precipitation in water (11.2 g; m.p. approximately 170° C.) is dissolved in boiling ethanol (200 cc). After 2 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with ethanol (2×10 cc) and dried at 40° C. under reduced pressure (0.067 kPa). N-(7-Phenoxy-1,8-naphthyridin-2-yl)cyclopropanecarboxamide (6.4 g) is produced, m.p. 190° C.

Workup

dissolutionis dissolved
customthe crystallised solid is separated by filtration
washwashed with ethanol (2×10 cc)
customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record: ord-19434691959c45ceaf8b8f7392c6e1d7
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04642308

Reaction notes

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