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-(5'-amino-2'-methyl-pyrrolidin-1-yl)-4-oxo-quinoline-3-carboxylic acid

HRID 11292Notes

Reaction equation

HRID 11292 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][CH:23]1[NH:27][CH:26]([CH3:28])[CH2:25][CH2:24]1>>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:27]2[CH:23]([NH2:22])[CH2:24][CH2:25][CH:26]2[CH3:28])[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[CH2:16][CH2:17]1

Participants

3

Reactant 2

HCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 219737405-Amino-2-methyl-pyrrolidine

Product 1

HCID 101776695-Amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(5'-amino-2'-methyl-pyrrolidin-1-yl)-4-oxo-quinoline-3-carboxylic acidYield 40%

Procedure

The condensation of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid with 5-amino-2-methyl-pyrrolidine in a similar manner as described in example 1 gave the titled product. Yield 40%, m.p 224–30° C., C18H20F2N4O3, m/z 379. (M+1)

Sources & evidence

ORD record
ord-d6518f5867684008afb4656f45b62e52
Source dataset
uspto-grants-2006_08
Patent number
US07098219B2

Reaction notes

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