Trifluoroacetic acid → 2-(6-methoxy-indazol-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

HRID 246501

반응식

HRID 246501 반응식
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=4)[CH:19]=[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>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=4)[CH:19]=[N:18]3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 71279780N-tert-butyl-2-(6-methoxy-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

생성물 1

HCID 712797232-(6-methoxy-indazol-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide수율 66%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of N-tert-butyl-2-(6-methoxy-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (130 mg, 263 μmol) in dichloromethane (3 mL) was added trifluoroacetic acid (1 mL). After 15 h, the mixture was concentrated in vacuo, add 25 mL Jan. 10, 1960 mixture of ammonium hydroxide/methanol/dichloromethane, stir for 1 hour. concentrated in vacuo. Purification by chromatography (silica, 24 g Analogix column, 0-4% methanol containing 10% ammonium hydroxide in dichloromethane) gave 2-(6-methoxy-indazol-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (63 mg, 66%). MS (M+H)+=365; 1H NMR (DMSO-d6) δ: 8.92 (s, 1H), 8.40 (d, J=5.1 Hz, 2H), 8.01 (s, 1H), 7.85 (d, J=8.9 Hz, 1H), 7.67 (s, 1H), 7.07 (dd, J=8.9, 2.0 Hz, 1H), 3.91 (s, 3H), 1.46 (s, 9H).

후처리

  1. concentrationthe mixture was concentrated in vacuo
  2. additionadd 25 mL Jan
  3. addition10, 1960 mixture of ammonium hydroxide/methanol/dichloromethane
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography (silica, 24 g Analogix column, 0-4% methanol containing 10% ammonium hydroxide in dichloromethane)

출처 및 근거

ORD 기록
ord-f863736c5e564053af26baba10edc6e6
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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