Sodium hydride → 6-[7a-(4-Cyano-benzyl)-3-(3,5-Dichlorophenyl)-2-oxo-2,3,5,6,7,7a-hexahydro-benzimidazol-3a-yl]-hexanoic acid ethyl ester

HRID 488744

反応式

HRID 488744 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]3=[CH:14][CH2:15][CH2:16][CH2:17][C:12]3([CH2:18][C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=3)[NH:11][C:10]2=[O:27])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].[Na+].[C:30]([O:37][CH2:38][CH3:39])(=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>CN(C=O)C>[CH2:38]([O:37][C:30](=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:13]12[CH2:14][CH2:15][CH2:16][CH2:17][C:12]1([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=1)[NH:11][C:10](=[O:27])[N:9]2[C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH3:39]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 31265Ethyl hexanoateHCID 104534514-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile

生成物 1

HCID 697862196-[7a-(4-Cyano-benzyl)-3-(3,5-Dichlorophenyl)-2-oxo-2,3,5,6,7,7a-hexahydro-benzimidazol-3a-yl]-hexanoic acid ethyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

4-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile (500 mg) (1.25 mmol) in DMF (20 ml) was carefully dropped on a suspension of NaH 60% (65 mg) (1.3 eq) in DMF (10 ml) at RT. The reaction mixture was stirred 1 h at RT, then ethyl hexanoate (0.27 ml) (1.2 eq) was added. After 3 h, the reaction mixture was poured on water and extracted with tBuOMe. The organic layer was washed with water, dried over Na2SO4 and concentrated. The residue was purified on SiO2 chromatography (eluent EtOAc/cyclohexane—2/8) to give 6-[7a-(4-Cyano-benzyl)-3-(3,5-Dichlorophenyl)-2-oxo-2,3,5,6,7,7a-hexahydro-benzimidazol-3a-yl]-hexanoic acid ethyl ester (200 mg) as an oil. 1H NMR (CDCl3): 7.55 (2H, d), 7.25 (2H, d), 7.1 (1H, m), 6.75 (2H, m), 4.95 (1H, m), 4.15 (2H, q), 3.7 (1H, m), 3.1 (1H, m), 3.0 (2H, s), 2.35 (2H, m), 2.2-1.3 (12H, m), 1.23 (3H, t).

後処理

  1. waitAfter 3 h
  2. additionthe reaction mixture was poured on water
  3. extractionextracted with tBuOMe
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified on SiO2 chromatography (eluent EtOAc/cyclohexane—2/8)

出典と根拠

ORDレコード
ord-648cb88e6eb14f0eb49bfd10be449dc3
出典データセット
uspto-grants-2005_12
特許番号
US06974815B2

関連ノート

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