Water → HCID 13983473, compound

HRID 580455Notes

Reaction equation

[CH3:1][N:2]([CH2:10][CH2:11][O:12][C:13]1[N:22]=[C:21]2[C:16]([CH:17]=[CH:18][C:19]([NH:23][C:24](=[O:33])[C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[N:20]2)=[CH:15][CH:14]=1)C(OC(C)(C)C)=O.O.[OH-].[Na+]>FC(F)(F)C(O)=O>[CH3:1][NH:2][CH2:10][CH2:11][O:12][C:13]1[N:22]=[C:21]2[C:16]([CH:17]=[CH:18][C:19]([NH:23][C:24](=[O:33])[C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)=[N:20]2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 4 °C

Procedure

A solution of N-{7-[2-(N-Methyl-N-tert-butoxycarbonylamino)ethoxy]-1,8-naphthyridin-2-yl}-4-methoxybenzamide (20 g) in trifluoroacetic acid (60 cc) is stirred for 1 hour at a temperature in the region of 20° C. The reaction mixture is poured into water (100 cc) and neutralized with 4N sodium hydroxide (180 cc). The insoluble product obtained is separated by filtration, washed with water and dried in the air, and is then dissolved in boiling acetonitrile (250 cc). After 2 hours' cooling at 4° C., the crystallized solid is separated by filtration, washed with acetonitrile (3×20 cc) and dried at 50° C. under reduced pressure (0.07 kPa). N-[7-(2-Methylaminoethoxy)-1,8-naphthyridin-2-yl]-4-methoxybenzamide (8.7 g), m.p. 146° C., is obtained.

Workup

customThe insoluble product obtained
customis separated by filtration
washwashed with water
customdried in the air
dissolutionis then dissolved
customthe crystallized solid is separated by filtration
washwashed with acetonitrile (3×20 cc)
customdried at 50° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record: ord-bbc89fb3ce314ed8a2a8b5ab56da1964
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04753933

Reaction notes

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