5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 5-Amino-7-[cis-3-amino-4-(1,2,3-triazol-1-yl)-pyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

HRID 1742943Notes

Reaction equation

HRID 1742943 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][C@H:23]1[C@@H:27]([N:28]2[CH:32]=[CH:31][N:30]=[N:29]2)[CH2:26][NH:25][CH2:24]1>>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:25]2[CH2:26][C@H:27]([N:28]3[CH:32]=[CH:31][N:30]=[N:29]3)[C@H:23]([NH2:22])[CH2:24]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 70283180rac-(3R,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidin-3-amine

Product 1

HCID 702836805-Amino-7-[cis-3-amino-4-(1,2,3-triazol-1-yl)-pyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acidYield 65%

Procedure

Prepared by following the same procedure as described for Example 17 by using 5-amino-1-cyclopropyl -6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid and cis-3-amino-4-(1,2,3-triazol-1-yl)pyrrolidine. Yield: 65%, m.p. 275°-277° C. 1H NMR (TFA) δ: 1.33-1.50 (m, 4H), 4.32-5.12 (m, 6H), 6.34 (m, 1H), 8.64 (s, 1H), 8.89 (s, 1H), 9.16 (s, 1H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-4c0af04fe7e144909479fde44010470a
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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