Methylamine → 1-(6-Amino-3,5-difluoropyridin-2-yl)-6,8-difluoro-7-methylamino-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

HRID 369231Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15](F)[C:16]=3[F:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[C:5]([F:25])=[CH:4][C:3]=1[F:26].[CH3:27][NH2:28]>N1C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15]([NH:28][CH3:27])[C:16]=3[F:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[C:5]([F:25])=[CH:4][C:3]=1[F:26]

Participants

Conditions

Temperature: 40 °C

Procedure

1-(6-Amino-3,5-difluoropyridin-2-yl)-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (60 mg) and a 40% aqueous solution (110 mg) of methylamine were added to pyridine (1,160 mg), and the mixture was stirred at 40° C. for 16 hours. The solvent was distilled off under reduced pressure, and ethanol (1 ml) was added to the residue. Deposits were collected by filtration and washed successively with ethanol and diisopropyl ether to obtain the title compound (58 mg) as a colorless powder.

Workup

distillationThe solvent was distilled off under reduced pressure, and ethanol (1 ml)
additionwas added to the residue
filtrationDeposits were collected by filtration
washwashed successively with ethanol and diisopropyl ether

Sources & evidence

ORD record: ord-6a15f65a343d4c7baec8f071fdfafde2
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136823

Reaction notes

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