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 1742934ノート

反応式

HRID 1742934 の反応式
[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]

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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.

出典と根拠

ORDレコード
ord-e6894de9033047239a4f868fa1528cd7
出典データセット
uspto-grants-1994_08
特許番号
US05342846

反応ノート

読み込み中…