5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 5-Amino-7-[3-[4-(aminomethyl)phenyl]-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 54476Notes

Reaction equation

HRID 54476 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.CC([N:26]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]2[CH2:41][CH2:40][NH:39][CH2:38]2)=[CH:33][CH:32]=1)C(=O)[O-])(C)C>>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:39]2[CH2:40][CH2:41][CH:37]([C:34]3[CH:35]=[CH:36][C:31]([CH2:30][NH2:26])=[CH:32][CH:33]=3)[CH2:38]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[CH2:16][CH2:17]1

Participants

3

Reactant 2

HCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 867469861,1-Dimethylethyl[[4-(3-pyrrolidinyl)phenyl]methyl]carbamate

Product 1

HCID 152884315-Amino-7-[3-[4-(aminomethyl)phenyl]-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Procedure

Starting from 5-amino-1-cyclopropyl-6, 7, 8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.95 g, 3.2 mmol) and 1,1-dimethylethyl[[4-(3-pyrrolidinyl) phenyl]methyl]carbamate, a procedure analogous to that given in Example 6 provided the title compound (0.75 g) as a yellow solid, mp 225°-227° C.

Sources & evidence

ORD record
ord-ab743c0ea2254af6b9ea01e27cfe52ba
Source dataset
uspto-grants-1997_04
Patent number
US05622966

Reaction notes

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