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Borane;tetrahydrofuran → 3-[4-chloro-2-{[6-(dimethylamino)-4-methylpyridin-3-yl]amino}-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]propan-1-ol

HRID 1398901
ノート
印刷プレビュー

反応式

HRID 1398901 の反応式
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([N:11]([C:19]3[CH:20]=[N:21][C:22]([N:26]([CH3:28])[CH3:27])=[CH:23][C:24]=3[CH3:25])C(=O)OC(C)(C)C)[N:7]([CH2:29][CH:30]=C)[C:6]=2[C:5]([CH:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[CH:4][CH:3]=1.B.[O:38]1CCC[CH2:39]1.O.O.O.O.B(O[O-])([O-])[O-].[Na+].[Na+].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:19]3[CH:20]=[N:21][C:22]([N:26]([CH3:28])[CH3:27])=[CH:23][C:24]=3[CH3:25])[N:7]([CH2:29][CH2:30][CH2:39][OH:38])[C:6]=2[C:5]([CH:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 2723981Borane;tetrahydrofuranHCID 18380057Sodium peroxyborate tetrahydrateHCID 86632906tert-Butyl [4-chloro-7-(1-ethylpropyl)-1-prop-2-en-1-yl-1H-benzimidazol-2-yl][6-(dimethylamino)-4-methylpyridin-3-yl]carbamate

生成物 1

HCID 687713093-[4-chloro-2-{[6-(dimethylamino)-4-methylpyridin-3-yl]amino}-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]propan-1-ol収率 29.5%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl [4-chloro-7-(1-ethylpropyl)-1-prop-2-en-1-yl-1H-benzimidazol-2-yl][6-(dimethylamino)-4-methylpyridin-3-yl]carbamate (450 mg, 0.88 mmol) in tetrahydrofuran (8.8 mL) was added borane-tetrahydrofuran complex (1.18 M in tetrahydrofuran, 7.46 mL, 8.8 mmol) at room temperature. After stirring for 2 hr, the mixture was poured into a suspension of sodium peroxyborate tetrahydrate (2.03 g, 13.2 mmol) in water (10 mL). The mixture was stirred for 14 hr at room temperature. The mixture was extracted with ethyl acetate. Organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was dissolved in methanol (5 mL) followed by addition of 6 N hydrochloric acid (5 mL). After stirring for 14 hr at room temperature, aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate. Organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture to give the title compound (110 mg, 0.26 mmol, 29%) as a colorless solid.

後処理

  1. stirringThe mixture was stirred for 14 hr at room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washOrganic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in methanol (5 mL)
  7. additionfollowed by addition of 6 N hydrochloric acid (5 mL)
  8. stirringAfter stirring for 14 hr at room temperature
  9. additionaqueous sodium bicarbonate was added
  10. extractionthe mixture was extracted with ethyl acetate
  11. washOrganic layer was washed with brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationconcentrated in vacuo
  14. customThe residue was purified by flash chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture

出典と根拠

ORDレコード
ord-ec539100ce0c45f69f865aa3cd7d8937
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08901141B2

反応ノート

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