Triethylamine → Methanesulfonic acid 2-oxo-1-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]-pyrrolidin-3-ylmethyl ester

HRID 1162924ノート

反応式

HRID 1162924 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[OH:13][CH2:14][CH:15]1[CH2:19][CH2:18][N:17]([C:20]2[CH:29]=[C:28]3[C:23]([CH:24]=[C:25]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[C:37]([F:40])([F:39])[F:38])[NH:26][C:27]3=[O:30])=[CH:22][CH:21]=2)[C:16]1=[O:41].[Cl-].[NH4+]>ClCCl>[O:41]=[C:16]1[CH:15]([CH2:14][O:13][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:19][CH2:18][N:17]1[C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[C:25]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:37]([F:40])([F:38])[F:39])[NH:26][C:27]2=[O:30])=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 118549597-(3-hydroxymethyl-2-oxopyrrolidin-1-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

生成物 1

HCID 86626744Methanesulfonic acid 2-oxo-1-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]-pyrrolidin-3-ylmethyl ester収率 40%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-20 °C

実験手順

Methanesulfonyl chloride (0.023 ml, 0.299 mmol) and triethylamine (0.03 ml, 0.299 mmol) were added at −20° C. to a dichloromethane solution (2 ml) that contained the 7-(3-hydroxymethyl-2-oxopyrrolidin-1-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (80 mg, 199 mmol) obtained in Example 1-46. The obtained mixture was stirred at −20° C. for 2 hours. Thereafter, a saturated ammonium chloride aqueous solution was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was then distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=30:1->20:1), so as to obtain methanesulfonic acid 2-oxo-1-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]-pyrrolidin-3-ylmethyl ester (38 mg, 40%) in the form of a colorless oil substance.

後処理

  1. extractionthe obtained mixture was then extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. distillationthe solvent was then distilled away under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=30:1->20:1)

出典と根拠

ORDレコード
ord-e5ad0d6e08e54926a9b6d87a0285a3bb
出典データセット
uspto-grants-2010_10
特許番号
US07820693B2

反応ノート

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