Water → (RS)-7-fluoro-8-{3-[4-(2-hydroxyethoxy)phenyl]-1-piperazinyl}-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

HRID 344866Notes

Reaction equation

[F:1][C:2]1[C:20](F)=[CH:19][C:5]2=[N:6][C:7]3[N:8]([CH3:18])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1.[OH:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]2[CH2:37][NH:36][CH2:35][CH2:34][NH:33]2)=[CH:28][CH:27]=1.O>CS(C)=O>[F:1][C:2]1[C:20]([N:36]2[CH2:35][CH2:34][NH:33][CH:32]([C:29]3[CH:28]=[CH:27][C:26]([O:25][CH2:24][CH2:23][OH:22])=[CH:31][CH:30]=3)[CH2:37]2)=[CH:19][C:5]2=[N:6][C:7]3[N:8]([CH3:18])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid (1.015 g) and (RS)-2-[4-(2-hydroxyethoxy)phenyl]-piperazine (1.7 g) in dimethyl sulphoxide (15 cc) is heated with stirring to a temperature in the region of 100° C. for 2 hours and a half. After cooling to approximately 20° C., the suspension is treated with water (30 cc), drained and washed with water (3×10 cc). After one recrystallization in dimethylformamide (15 cc), (RS)-7-fluoro-8-{3-[4-(2-hydroxyethoxy)phenyl]-1-piperazinyl}-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid (1.2 g)is obtained in the form of a yellow solid, m.p. 276° C.

Workup

temperatureis heated
temperatureAfter cooling to approximately 20° C.
washwashed with water (3×10 cc)
customAfter one recrystallization in dimethylformamide (15 cc)

Sources & evidence

ORD record: ord-58749b7b654c4112b4e5ac33e8db4e34
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053509

Reaction notes

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