Ethyl 6,8-difluoro-1-(4-fluorophenyl)-7-[3-(1,2,3-triazol-1-yl)-pyrrolidin-1-yl]-1,4-dihydro-4-oxo-quinoline-3-carboxylate → 6,8-Difluoro-1-(4-fluorophenyl)-7-[3-(1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

HRID 1742934Notes

Reaction equation

HRID 1742934 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:22])[C:11]=1[N:12]1[CH2:16][CH2:15][CH:14]([N:17]3[CH:21]=[CH:20][N:19]=[N:18]3)[CH2:13]1)[N:8]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[CH:7]=[C:6]([C:30]([O:32]CC)=[O:31])[C:5]2=[O:35]>[OH-].[Na+].C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:22])[C:11]=1[N:12]1[CH2:16][CH2:15][CH:14]([N:17]3[CH:21]=[CH:20][N:19]=[N:18]3)[CH2:13]1)[N:8]([C:23]1[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=1)[CH:7]=[C:6]([C:30]([OH:32])=[O:31])[C:5]2=[O:35]

Participants

4

Reactant 1

HCID 15228836Ethyl 6,8-difluoro-1-(4-fluorophenyl)-7-[3-(1,2,3-triazol-1-yl)-pyrrolidin-1-yl]-1,4-dihydro-4-oxo-quinoline-3-carboxylate

Product 1

HCID 190060126,8-Difluoro-1-(4-fluorophenyl)-7-[3-(1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of ethyl 6,8-difluoro-1-(4-fluorophenyl)-7-[3-(1,2,3-triazol-1-yl)-pyrrolidin-1-yl]-1,4-dihydro-4-oxo-quinoline-3-carboxylate (180 mg, 0.37 mmol) in 20 ml NaOH solution (containing 15 mg NaOH) and THF (20 ml) was heated at 90° C. for 3.5 h. The THF was evaporated and the separated solid was redissolved in water layer by heating and acidified to pH 6.0. The precipitate was filtered, washed with water and dried in vac-oven at 40° C., gave the title compound as a light yellow solid. Yield: 89 mg, 52.7%; m.p. 303° C. 1H NMR (TFA) δ: 2.82 (m, 2H), 4.14-4.64 (m, 4H), 5.74 (m, 1H), 7.37 (m, 2H), 7.60 (m, 2H), 8.20 (dd, 1H), 8.54 (d, 1H), 8.65 (d, 1H), 9.03 (s, 1H).

Workup

  1. customThe THF was evaporated
  2. dissolutionthe separated solid was redissolved in water layer
  3. temperatureby heating
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried in vac-oven at 40° C.

Sources & evidence

ORD record
ord-e6894de9033047239a4f868fa1528cd7
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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