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Trifluoroacetic acid → 6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-amine

HRID 1628039
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HRID 1628039 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:29]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:16]2=[N:17][CH:18]=[C:19]([NH:21]C(=O)OC(C)(C)C)[N:20]=[C:15]2[CH:14]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:29]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:35])([CH3:37])[CH3:36])[C:16]2=[N:17][CH:18]=[C:19]([NH2:21])[N:20]=[C:15]2[CH:14]=1
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참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acid2회HCID 67216771tert-butyl 6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate

생성물 1

HCID 583821536-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-amine수율 40.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 8857
Ethyl Acetate
용매

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온도
30 °C

실험 절차

In a flask was added tert-butyl 6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate (0.200 g, 0.382 mmol) and TFA (0.088 mL, 1.15 mmol) in DCM (1 mL). The mixture was stirred for about 2 h at about 30° C. Additional TFA (0.100 mL, 1.29 mmol) was added and the mixture was stirred at about 40° C. overnight. The mixture was diluted with EtOAc (10 mL) and washed with saturated aqueous Na2CO3 (5 mL) and dried over MgSO4, filtered and concentrated in vacuo. The material was purified by 4 g silica column eluting with 10 to 100% EtOAc/DCM to provide 6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-amine (0.065 g, 40%): LC/MS (Table 2, c) Rt=1.62 min; MS m/z 424 (M+H)+.

후처리

  1. stirringthe mixture was stirred at about 40° C. overnight
  2. washwashed with saturated aqueous Na2CO3 (5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe material was purified by 4 g silica column
  7. washeluting with 10 to 100% EtOAc/DCM

출처 및 근거

ORD 기록
ord-bd0a20ad00c8479486c005e668117739
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785639B2

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