Sodium Bicarbonate → 2-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-4-carboxylic acid methyl ester

HRID 18619

反応式

HRID 18619 の反応式
[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14](Cl)(Cl)Cl)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].Cl.Cl.[CH:20]([N:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1)([CH3:22])[CH3:21].C([O-])(O)=[O:31].[Na+]>C1COCC1.O>[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14](=[O:31])[NH:29][CH:26]3[CH2:27][CH2:28][N:23]([CH:20]([CH3:22])[CH3:21])[CH2:24][CH2:25]3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 177503401-(Propan-2-yl)piperidin-4-amine dihydrochlorideHCID 23033456Methyl-2-trichloromethyl-1H-benzoimidazole-4-carboxylate

生成物 1

HCID 686161592-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-4-carboxylic acid methyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 3.99 g (13.6 mmol) 2-trichloromethyl-1H-benzoimidazole-4-carboxylic acid methyl ester in 40 mL THF was added slowly to a mixture of 2.9 g (13.6 mmol) 1-isopropyl-piperidin-4-ylamine-dihydrochloride and 13.7 g (0.163 mol, 12 equivalents) NaHCO3 in 200 mL THF and 120 mL water. The reaction mixture was stirred for 2 h at RT. The THF was distilled off. The resulting aqueous suspension was diluted with 200 mL CH2Cl2 and extracted twice with 150 mL water. The organic layer was concentrated under reduced pressure and the resulting residue was purified by flash-chromatography on silica gel using an ethyl acetate/methanol-(4:1)-mixture as eluent. The title compound was obtained as a light brown crystalline material.

後処理

  1. distillationThe THF was distilled off
  2. additionThe resulting aqueous suspension was diluted with 200 mL CH2Cl2
  3. extractionextracted twice with 150 mL water
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe resulting residue was purified by flash-chromatography on silica gel using an ethyl acetate/methanol-(4

出典と根拠

ORDレコード
ord-44f8c6df8ba24f0490d82b7e11209947
出典データセット
uspto-grants-2010_06
特許番号
US07741341B2

関連ノート

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