Ethanol → N-[7-(3-fluorophenoxy)-1,8-naphthyridin-2-yl]-4-methoxybenzamide

HRID 235829Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=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]=[C:26]([F:30])[CH:25]=3)=[CH:18][CH:19]=2)[N:14]=1.C(O)C>O>[F:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[O:23][C:17]1[N:16]=[C:15]2[C:20]([CH:21]=[CH:22][C:13]([NH:12][C:7](=[O:9])[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)=[N:14]2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with 4-methoxybenzoic acid (6.1 g), N,N'-carbonyldiimidazole (6.5 g) and 2-amino-7-(3-fluorophenoxy)-1,8-naphthyridine (7.65 g). The product produced by precipitation in water (14 g) is dissolved in boiling ethanol (110 cc). After 2 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with ethanol (2×10 cc) and dried at 45° C. at reduced pressure (0.067 kPa). N-[7-(3-fluorophenoxy)-1,8-naphthyridin-2-yl]-4-methoxybenzamide (7 g) is produced, m.p. 151° C.

Workup

dissolutionis dissolved
customthe crystallised solid is separated by filtration
washwashed with ethanol (2×10 cc)
customdried at 45° C. at reduced pressure (0.067 kPa)

Sources & evidence

ORD record: ord-5f51614bf97347878b736a3f7982d885
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04642308

Reaction notes

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