Lithium borohydride → HCID 68770584、化合物

HRID 1398755ノート

反応式

HRID 1398755 の反応式
[BH4-].[Li+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[N:16]([CH2:17][CH2:18][C:19](OCC)=[O:20])[C:15]2[C:24]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:25][CH:26]=[CH:27][C:14]=2[N:13]=1>O1CCCC1.[Cl-].[NH4+].C(=O)([O-])O.[Na+]>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[N:16]([CH2:17][CH2:18][CH2:19][OH:20])[C:15]2[C:24]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:25][CH:26]=[CH:27][C:14]=2[N:13]=1

参加物

6

反応物 2

HCID 4148881Lithium borohydrideHCID 68761561HCID 68761561、化合物

生成物 1

HCID 68770584HCID 68770584、化合物収率 25.4%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
0 °C

実験手順

To a suspension of lithium borohydride (22.5 mg, 1.03 mmol) in tetrahydrofuran (3.5 mL) was added ethyl 3-[2-[(2,4-dichlorophenyl)amino]-7-(diethylamino)-1H-benzimidazol-1-yl]propanoate (Reference Example 28; 155 mg, 0.345 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 20 hr, the mixture was diluted with aqueous ammonium chloride at 0° C. and stirred at 0° C. for 30 min. The resultant mixture was diluted with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 25% ethyl acetate/n-hexane mixture to give the title compound as a solid (35.7 mg, 0.0876 mmol, 25%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 25% ethyl acetate/n-hexane mixture

出典と根拠

ORDレコード
ord-2c1cb4ffc0c941c395b779f3c2905c98
出典データセット
uspto-grants-2014_12
特許番号
US08901141B2

反応ノート

読み込み中…