Triethylamine → (RS)-7-fluoro-1-methyl-4-oxo-8-(3-phenyl-1-piperazinyl)-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

HRID 344845

Reaction equation

Cl[C:2]1[C:3]([F:21])=[CH:4][C:5]2[C:6]([CH:20]=1)=[N:7][C:8]1[N:9]([CH3:19])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.[C:22]1([CH:28]2[CH2:33][NH:32][CH2:31][CH2:30][NH:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>N1C=CC=CC=1>[F:21][C:3]1[C:2]([N:32]2[CH2:31][CH2:30][NH:29][CH:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:33]2)=[CH:20][C:6]2=[N:7][C:8]3[N:9]([CH3:19])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=3[CH:14]=[C:5]2[CH:4]=1

Participants

Conditions

Temperature: 115 °C

Procedure

A suspension of 8-chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid (1.84 g) in pyridine (20 cc), (RS)-2-phenylpiperazine (5.83 g) and triethylamine (1.24 g) is heated to a temperature in the region of 115° C. for 5 hours. After cooling to approximately 20° C., the precipitate formed is drained and washed with pyridine (2×5 cc), isopropyl alcohol (2×5 cc), ethanol (2×5 cc) and ethyl ether (1×20 cc). After 1 recrystallization in a mixture of dimethylformamide (40 cc) and ethanol (40 cc), (RS)-7-fluoro-1-methyl-4-oxo-8-(3-phenyl-1-piperazinyl)-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid (0.920 g) is obtained in the form of a yellow solid, m.p. 265° C.

Workup

temperatureAfter cooling to approximately 20° C.
customthe precipitate formed
washwashed with pyridine (2×5 cc), isopropyl alcohol (2×5 cc), ethanol (2×5 cc) and ethyl ether (1×20 cc)
customAfter 1 recrystallization
additionin a mixture of dimethylformamide (40 cc) and ethanol (40 cc)

Sources & evidence

ORD record: ord-da4a0a6f37b1432da53cb69c5b8b0d02
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053509

Linked notes

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