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

HRID 610292Notes

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.C(O)(=O)C.C(O)(=O)C.[CH3:42][NH:43][CH:44]1[CH2:47][NH:46][CH2:45]1.CN1CCCC1>C(OCC)C>[NH2:7][C:8]1[C:17]([F:18])=[C:16]([N:46]2[CH2:47][CH:44]([NH:43][CH3:42])[CH2:45]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-difluoropyridin-2-yl) -8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 80 mg of 3-methylaminoazetidine diacetate, and 250 mg of N-methylpyrrolidine, and the mixture was stirred at 100° C. for 10 minutes. After adding 5 ml of diethylether, the mixture was stirred and allowed to cool 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 72 mg of the title compound as a yellow powder.

Workup

stirringthe mixture was stirred
temperatureto cool 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-18af41378b07451b8242d6699cb8b0c3
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998436

Reaction notes

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