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-[4-[(methylamino)methyl]phenyl]-1-pyrrolidinyl]-4-oxo-3-quinolinecarboxylic acid

HRID 1588310Notes

Reaction equation

HRID 1588310 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.[CH3:22][NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[CH2:35][CH2:34][NH:33][CH2:32]2)=[CH:27][CH:26]=1>>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:33]2[CH2:34][CH2:35][CH:31]([C:28]3[CH:29]=[CH:30][C:25]([CH2:24][NH:23][CH3:22])=[CH:26][CH:27]=3)[CH2:32]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 15288435N-methyl-4-(3-pyrrolidinyl)benzenemethanamine

Product 1

HCID 152884375-Amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-[3-[4-[(methylamino)methyl]phenyl]-1-pyrrolidinyl]-4-oxo-3-quinolinecarboxylic acidYield 51%

Procedure

Starting from 5-amino-1-cyclopropyl 6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.89 g, 3.0 mmol) and N-methyl-4-(3-pyrrolidinyl)benzenemethanamine, a procedure analogous to that given in Example 1 provided the title compound (0.71 g, 51%) as a yellow solid, mp 201°-205° C.

Sources & evidence

ORD record
ord-b1d71c4196e3460ca0f46d08d8b49854
Source dataset
uspto-grants-1993_06
Patent number
US05221676

Reaction notes

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