Lithium borohydride → HCID 68770584, 화합물

HRID 1398755노트

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HRID 1398755 반응식
[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

참가 물질

6

반응물 2

HCID 4148881Lithium borohydrideHCID 68761561HCID 68761561, 화합물

생성물 1

HCID 68770584HCID 68770584, 화합물수율 25.4%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 25517Ammonium Chloride용매HCID 516892Sodium Bicarbonate용매

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-2c1cb4ffc0c941c395b779f3c2905c98
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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