5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 5-Amino-1-(cyclopropyl)-6,8-difluoro-1,4-dihydro-7-(3'-aminomethyl-4'-hydroxy-piperidin-1-yl)-4-oxo-quinoline-3-carboxylic acid

HRID 11298Notes

Reaction equation

HRID 11298 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[NH2:22][CH2:23][CH:24]1[CH:29]([OH:30])[CH2:28][CH2:27][NH:26][CH2:25]1>>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:26]2[CH2:27][CH2:28][CH:29]([OH:30])[CH:24]([CH2:23][NH2:22])[CH2:25]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 216153883-(Aminomethyl)piperidin-4-ol

Product 1

HCID 867602185-Amino-1-(cyclopropyl)-6,8-difluoro-1,4-dihydro-7-(3'-aminomethyl-4'-hydroxy-piperidin-1-yl)-4-oxo-quinoline-3-carboxylic acidYield 52.8%

Procedure

The condensation of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid with 3-aminomethyl-4-hydroxy-piperidine was carried out in a similar manner as described in example 1, gave the titled product. Yield 52.8%, m.p 202–04° C., C19H22F2N4O4, m/z 409 (M+1).

Sources & evidence

ORD record
ord-db8fe1955bfb44b1ad634f8887301c0b
Source dataset
uspto-grants-2006_08
Patent number
US07098219B2

Reaction notes

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