Pyridine → 5-Amino-1-(6-amino-3,5-difluoropyridine-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyaminoazetidine-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 368517Notes

Reaction equation

N1C=CC=CC=1.[NH2:7][C:8]1[C:17]([F:18])=[C:16](F)[C:15]([Cl:20])=[C:14]2[C:9]=1[C:10](=[O:33])[C:11]([C:30]([OH:32])=[O:31])=[CH:12][N:13]2[C:21]1[C:26]([F:27])=[CH:25][C:24]([F:28])=[C:23]([NH2:29])[N:22]=1.Cl.[OH:35][NH:36][CH:37]1[CH2:40][NH:39][CH2:38]1.CN1CCCC1>C(OCC)C>[NH2:7][C:8]1[C:17]([F:18])=[C:16]([N:39]2[CH2:40][CH:37]([NH:36][OH:35])[CH2:38]2)[C:15]([Cl:20])=[C:14]2[C:9]=1[C:10](=[O:33])[C:11]([C:30]([OH:32])=[O:31])=[CH:12][N:13]2[C:21]1[C:26]([F:27])=[CH:25][C:24]([F:28])=[C:23]([NH2:29])[N:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 300 mg of pyridine were added 120 mg of 5-amino-1-(6-amino-3,5-difluoropyridine-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 80 mg of 3-hydroxyaminoazetidine hydrochloride, and 250 mg of N-methylpyrrolidine, and the mixture was stirred at 100° C. for 3 minutes. After adding 5 ml of diethylether, the mixture was allowed to stand for 1 hour and decanted. 2 ml of ethanol was added and the mixture was stirred. The precipitate was collected by filtration and washed with ethanol and diethylether successively to obtain 64 mg of the title compound as a yellow powder.

Workup

waitto stand for 1 hour
customdecanted
addition2 ml of ethanol was added
stirringthe mixture was stirred
filtrationThe precipitate was collected by filtration
washwashed with ethanol and diethylether successively

Sources & evidence

ORD record: ord-846c872e892d4632ab2d7ffcb8bd3d4b
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06133284

Reaction notes

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