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

HRID 1742941

Reaction equation

HRID 1742941 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:26])[C:5]([C:23]([OH:25])=[O:24])=[CH:6][N:7]2[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22].Cl.[N:28]1([CH:33]2[CH2:37][CH2:36][NH:35][CH2:34]2)[CH:32]=[CH:31][N:30]=[N:29]1.N1(C2CCCCCCCCCC2)CCCCCCCCCN1>C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:35]2[CH2:36][CH2:37][CH:33]([N:28]3[CH:32]=[CH:31][N:30]=[N:29]3)[CH2:34]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:26])[C:5]([C:23]([OH:25])=[O:24])=[CH:6][N:7]2[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22]

Participants

5

Reactant 3

HCID 148965525-Amino-1-(2,4-difluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acidHCID 19005943HCID 19005943, compoundHCID 57346892Diazabicycloundecane

Product 1

HCID 99133645-Amino-1-(2,4-difluorophenyl)-6,8-difluoro-7-[3-(1,2,3-triazol-1-yl]pyrrolidin-1-yl]-1,4-dihydro-4-oxo-quinoline-3-carboxylic acidYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-amino-1-(2,4-difluorophenyl) -6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (200 mg, 0.54 mmol), 3-(1,2,3-triazol-1-yl)pyrrolidine hydrochloride (231 mg, 1.25 mmol) and diazabicycloundecane (200 mg, 1.31 mmol) in acetonitrile (25 ml) was refluxed for 45 h. The separated solid was filtered, washed with acetonitrile and ether to give 150 mg (57%) of desired product, m.p. 307.5°-309° C. 1H NMR (TFA) δ: 2.81 (m, 2H), 4.06-4.53 (m, 4H), 5.73 (m, 1H), 7.15-7.23 (m, 2H), 7.59-7.66 (m, 1H), 8.52 (d, 1H), 8.62 (d, 1H), 8.82 (d, 1H).

Workup

  1. temperaturewas refluxed for 45 h
  2. filtrationThe separated solid was filtered
  3. washwashed with acetonitrile and ether

Sources & evidence

ORD record
ord-01aa3e14f04b4026b239b7443c1624c3
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Linked notes

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