1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid → 1-Cyclopropyl-6-fluoro-1,4-dihydro-7-[3-[4-[(methylamino) methyl]phenyl]-1-pyrrolidinyl]-4-oxo-3-quinolinecarboxylic acid

HRID 54478

Reaction equation

HRID 54478 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:20][NH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]2[CH2:33][CH2:32][NH:31][CH2:30]2)=[CH:25][CH:24]=1>>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([N:31]4[CH2:32][CH2:33][CH:29]([C:26]5[CH:27]=[CH:28][C:23]([CH2:22][NH:21][CH3:20])=[CH:24][CH:25]=5)[CH2:30]4)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 15288435N-methyl-4-(3-pyrrolidinyl)benzenemethanamine

Product 1

HCID 152884361-Cyclopropyl-6-fluoro-1,4-dihydro-7-[3-[4-[(methylamino) methyl]phenyl]-1-pyrrolidinyl]-4-oxo-3-quinolinecarboxylic acidYield 85%

Procedure

Starting from 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.80 g, 3.0 mmol) and N-methyl-4-(3-pyrrolidinyl)benzene-methanamine, a procedure analogous to that given in Example 1 provided the title compound (1.11 g, 85%) as an off-white solid, mp 235°-237° C.

Sources & evidence

ORD record
ord-1852f2c77e5740aab35b1c6110db6dc1
Source dataset
uspto-grants-1997_04
Patent number
US05622966

Linked notes

Loading…