Trifluoroacetic acid → N-tert-butyl-2-(5-(difluoromethoxy)-1-(2-(4-methylpiperazin-1-yl)-2-oxoethyl)-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246537

반응식

HRID 246537 반응식
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH:27]([F:29])[F:28])[CH:24]=4)[N:19]([CH2:30][C:31]([N:33]4[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]4)=[O:32])[N:18]=3)[N:15]=2)[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.ClCCl.CO>ClCCl>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH:27]([F:29])[F:28])[CH:24]=4)[N:19]([CH2:30][C:31]([N:33]4[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]4)=[O:32])[N:18]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 21226129Dichloromethane methanolHCID 71280481N-tert-butyl-2-(5-(difluoromethoxy)-1-(2-(4-methylpiperazin-1-yl)-2-oxoethyl)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

생성물 1

HCID 71280594N-tert-butyl-2-(5-(difluoromethoxy)-1-(2-(4-methylpiperazin-1-yl)-2-oxoethyl)-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide수율 66,559.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

To a stirred solution of N-tert-butyl-2-(5-(difluoromethoxy)-1-(2-(4-methylpiperazin-1-yl)-2-oxoethyl)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (41.7 mg, 62.2 μmol) in dichloromethane (3 mL) under Ar trifluoroacetic acid (208 mg, 0.140 mL, 1.83 mmol) was added at 25° C. After 18 h, the reaction was concentrated in vacuo to give a yellow residue. The residue was dissolved in a mix of dichloromethane/methanol/NH3OH (3:2:0.25, 5.25 mL) and stirred at 25° C. After 2.5 h, the material was concentrated and dried in vacuo (200 mTorr, 40° C.) to give N-tert-butyl-2-(5-(difluoromethoxy)-1-(2-(4-methylpiperazin-1-yl)-2-oxoethyl)-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (22.4 mg, 41.4 mmol, 67%) as a yellow solid. MS (M)'=541; 1H NMR (DMSO-d6) δ: 12.84 (d, J=2.8 Hz, 1H), 9.02 (s, 1H), 8.41 (d, J=3.0 Hz, 1H), 8.23 (d, J=2.3 Hz, 1H), 7.89 (s, 1H), 7.75 (d, J=9.3 Hz, 1H), 7.41 (dd, J=2.3, 9.0 Hz, 1H), 7.21 (t, J=74.5 Hz, 1H), 5.71 (br. s, 2H), 3.82 (br. s, 2H), 3.50 (br. s, 2H), 2.74 (br. s, 2H), 2.67 (br. s, 2H), 2.33 (s, 3H), 1.51 (s, 9H).

후처리

  1. concentrationthe reaction was concentrated in vacuo
  2. customto give a yellow residue
  3. dissolutionThe residue was dissolved in
  4. waitAfter 2.5 h
  5. concentrationthe material was concentrated
  6. customdried in vacuo (200 mTorr, 40° C.)

출처 및 근거

ORD 기록
ord-6a89ceffbeb244bd9f6aa692559b9f5a
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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