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

HRID 11297Notes

Reaction equation

HRID 11297 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[NH2:22][CH2:23][CH:24]1[CH:29]([OH:30])[CH2:28][CH2:27][NH:26][CH2:25]1>>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:17])[C:10]([F:16])=[C:11]([N:26]4[CH2:27][CH2:28][CH:29]([OH:30])[CH:24]([CH2:23][NH2:22])[CH2:25]4)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 146512581-Cyclopropyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 216153883-(Aminomethyl)piperidin-4-ol

Product 1

HCID 219737551-Cyclopropyl-6,8-difluoro-5-methyl-1,4-dihydro-7-(3'-aminomethyl-4'-hydroxy-piperidin-1-yl)-4-oxo-quinoline-3-carboxylic acidYield 45.9%

Procedure

The condensation of 1-cyclopropyl-6,7,8-trifluoro-5-methyl-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 45.9%, m.p 270–75° C., C20H23F2N3O4, m/z 408 (M+1).

Sources & evidence

ORD record
ord-76d3fc7e5e284b0d87498917e0b85970
Source dataset
uspto-grants-2006_08
Patent number
US07098219B2

Reaction notes

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