Lithium Hydroxide → 2-(4-(pyrrolidin-1-ylmethyl)-2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid

HRID 85189ノート

反応式

HRID 85189 の反応式
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[NH:17][C:16]4[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([O:24]C)=[O:23])[C:15]=4[N:14]=3)=[C:9]([C:26]([F:29])([F:28])[F:27])[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-]>C1COCC1.O>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[NH:17][C:16]4[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([OH:24])=[O:23])[C:15]=4[N:14]=3)=[C:9]([C:26]([F:28])([F:27])[F:29])[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 67201270Methyl 2-(4-(pyrrolidin-1-ylmethyl)-2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylate

生成物 1

HCID 672021382-(4-(pyrrolidin-1-ylmethyl)-2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid収率 40%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

Methyl 2-(4-(pyrrolidin-1-ylmethyl)-2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylate (544 mg) and LiOH (95 mg, 4 mmol) were dissolved in THF/H2O (1:1, 24 mL). The reaction was stirred overnight at room temperature, then heated at 50° C. overnight. The solvents were removed in vacuo. The residue was taken up in water and the pH was adjusted to 7-8 with 1N HCl. After allowing the mixture to stirred for 1 hour, the solids were collected by filtration to afford 2-(4-(pyrrolidin-1-ylmethyl)-2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid 159 as a pale solid (170 mg, 2-step yield: 40%). MS (ESI) calcd for C20H18F3N3O2: 389.14; found: 390 [M+H].

後処理

  1. temperatureheated at 50° C. overnight
  2. customThe solvents were removed in vacuo
  3. stirringto stirred for 1 hour
  4. filtrationthe solids were collected by filtration

出典と根拠

ORDレコード
ord-ec34ac6842424acda39db5cb438a7914
出典データセット
uspto-grants-2014_09
特許番号
US08846947B2

反応ノート

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