Lithium borohydride → HCID 58012359、化合物

HRID 1698574ノート

反応式

HRID 1698574 の反応式
C([O:4][C:5](=O)[CH2:6][N:7]1[C:11]2[C:12]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][CH:14]=[C:15]([Cl:16])[C:10]=2[N:9]=[C:8]1[NH:22][C:23]1[C:28]([CH3:29])=[CH:27][C:26]([Cl:30])=[CH:25][C:24]=1[O:31][CH3:32])(C)C.[BH4-].[Li+]>O1CCCC1.O>[Cl:16][C:15]1[C:10]2[N:9]=[C:8]([NH:22][C:23]3[C:28]([CH3:29])=[CH:27][C:26]([Cl:30])=[CH:25][C:24]=3[O:31][CH3:32])[N:7]([CH2:6][CH2:5][OH:4])[C:11]=2[C:12]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][CH:14]=1

参加物

5

反応物 2

HCID 4148881Lithium borohydrideHCID 58012354HCID 58012354、化合物

生成物 1

HCID 58012359HCID 58012359、化合物収率 62.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of isopropyl[4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate (453 mg, 0.920 mmol) in tetrahydrofuran (5 mL) was added lithium tetrahydroborate (60 mg, 2.76 mmol), and the mixture was refluxed for 2 hours. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The residual solid was recrystallized with ethyl acetate-n-hexane to give 250 mg (0.573 mmol, 62.3%) of the title compound as a colorless crystal. The filtrate was concentrated in vacuo, and the residual solid was recrystallized with ethyl acetate-hexane to give 91 mg (0.209 mmol, 22.7%) of the title compound as a colorless crystal.

後処理

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate (X2)
  4. washThe combined organic layer was washed with brine (X1)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residual solid was recrystallized with ethyl acetate-n-hexane

出典と根拠

ORDレコード
ord-c66c115ebabc40cd8f52c1c70a1dacd5
出典データセット
uspto-grants-2012_04
特許番号
US08163935B2

反応ノート

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