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 1742934노트

반응식

HRID 1742934 반응식
[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]

참가 물질

4

반응물 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

생성물 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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-e6894de9033047239a4f868fa1528cd7
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05342846

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