Ammonium formate → ethyl 3-(6-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate

HRID 1676018노트

반응식

HRID 1676018 반응식
[CH2:1]([O:3][C:4](=[O:25])[CH:5]=[C:6]([N:13]1[C:17]2[CH:18]=[CH:19][C:20]([N+:22]([O-])=O)=[CH:21][C:16]=2[N:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].[CH2:26]([O:28][C:29](=[O:50])[CH:30]=[C:31]([N:38]1[C:42]2[CH:43]=[C:44]([N+:47]([O-])=O)[CH:45]=[CH:46][C:41]=2[N:40]=[CH:39]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:27].C([O-])=O.[NH4+]>C(O)C.O.[Pd]>[NH2:47][C:44]1[CH:45]=[CH:46][C:41]2[N:40]=[CH:39][N:38]([CH:31]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:30][C:29]([O:28][CH2:26][CH3:27])=[O:50])[C:42]=2[CH:43]=1.[NH2:22][C:20]1[CH:19]=[CH:18][C:17]2[N:13]([CH:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:25])[CH:14]=[N:15][C:16]=2[CH:21]=1

참가 물질

8

반응물 3

HCID 2723923Ammonium formateHCID 67352746Ethyl-3-(5-nitro-1h-benzimidazol-1-yl)-3-phenyl-2-propenoateHCID 67353774Ethyl-3-(6-nitro-1h-benzimidazol-1-yl)-3-phenyl-2-propenoate

생성물 2

HCID 67351765ethyl 3-(6-amino-1H-benzimidazol-1-yl)-3-phenylpropanoateHCID 67351926ethyl 3-(5-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a mixture of ethyl-3-(5-nitro-1H-benzimidazol-1-yl)-3-phenyl-2-propenoate and ethyl-3-(6-nitro-1H-benzimidazol-1-yl)-3-phenyl-2-propenoate (5.34 g, 15.8 mmol) in a mixture of ethanol and water (10:1, 66 mL) was added palladium on carbon (801 mg, 10% w/w Pd) and ammonium formate (6.0 g, 95 mmol). The suspension was heated to reflux, and was stirred at this temperature for 1.5 hours. The reaction mixture was allowed to cool to room temperature, then filtered through Celite®, and the filter pad washed several times with ethanol. The combined filtrates were evaporated in vacuo, and the residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (99:1) to give, in order of elution, ethyl 3-(6-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate, [LCMS (Method A, Mobile Phase I) RT=3.33 min, MH+ 310] and ethyl 3-(5-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate (1.96 g), [LCMS (Method A, Mobile Phase I) RT=3.35 min, MH+ 310].

후처리

  1. temperatureThe suspension was heated
  2. temperatureto reflux
  3. filtrationfiltered through Celite®
  4. washthe filter pad washed several times with ethanol
  5. customThe combined filtrates were evaporated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel
  7. washeluting with a mixture of dichloromethane and methanol (99:1)

출처 및 근거

ORD 기록
ord-311afd4a87b14749aa867a06227778b2
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003806B2

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