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Ethylenediamine → 2-(1H-indol-7-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246439
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HRID 246439 반응식
C([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[CH:22]4)[N:15]=2)[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])(C)(C)C.C(N)CN>CN(C=O)C.O>[NH:24]1[C:25]2[C:21](=[CH:20][CH:19]=[CH:18][C:17]=2[C:14]2[N:15]=[C:16]3[C:8]([C:6]([NH2:5])=[O:7])=[CH:9][NH:10][C:11]3=[N:12][CH:13]=2)[CH:22]=[CH:23]1
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참가 물질

5

반응물 2

HCID 3301EthylenediamineHCID 71280445N-tert-butyl-2-(1H-indol-7-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

생성물 1

HCID 866779812-(1H-indol-7-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide수율 43.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a stirred solution of N-tert-butyl-2-(1H-indol-7-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (54 mg, 116 μmol) in DMF (3 mL) was added ethylenediamine (350 mg, 393 μL, 5.82 mmol) and the mixture heated at 60° C. After 72 h, the reaction mixture was cooled, diluted with water, and extracted into ethyl acetate. The organic phases were combined and washed with water and brine then dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated with ether, then water, diluted with dichloromethane, and finally the solvents removed in vacuo to give N-tert-butyl-2-(2-(1H-indol-7-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (14 mg). MS (M+H)+=334.1; 1H NMR (DMSO-d6) δ: 12.83 (br. s., 1H), 11.46 (br. s., 1H), 9.01 (s, 1H), 8.49 (s, 1H), 8.24 (s, 1H), 7.81 (d, J=7.8 Hz, 1H), 7.73 (d, J=7.5 Hz, 1H), 7.52 (br. s., 1H), 7.30 (t, J=7.5 Hz, 1H), 6.69 (br. s., 1H), 1.55 (s, 9H).

후처리

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted into ethyl acetate
  3. washwashed with water and brine
  4. dry with materialthen dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with ether
  8. additionwater, diluted with dichloromethane
  9. customfinally the solvents removed in vacuo

출처 및 근거

ORD 기록
ord-29749230fc9e4587bbc5ac0079aff843
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658646B2

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