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

HRID 246327노트

반응식

HRID 246327 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][C:22]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:23][CH:24]=4)[N:19]([CH3:30])[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.C(N)CN.O>ClCCl.C(OCC)(=O)C>[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][C:22]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:23][CH:24]=4)[N:19]([CH3:30])[N:18]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 962WaterHCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 712801592-(6-methanesulfonyl-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

생성물 1

HCID 712801302-(6-methanesulfonyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide수율 67%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

In a round-bottomed flask, 2-(6-methanesulfonyl-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (76 mg, 0.137 mmol) was dissolved in dichloromethane (0.7 ml) and trifluoroacetic acid (0.42 ml, 5.45 mmol) was added. The reaction mixture was stirred at room temperature for 2.5 h then concentrated. The residue was dissolved in dichloromethane (0.7 ml) and ethylenediamine (0.55 ml, 8.14 mmol) was added. The reaction was stirred at room temperature for 1 h then water and ethyl acetate were added. The resulting suspension was filtered and washed with hot water and ethyl acetate. The product collected was dried under high vacuum to provide 39 mg (67%) of 2-(6-methanesulfonyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a light yellow powder. MS: (2M+Na)+=875; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 12.89 (br. s, 1H), 9.13 (s, 1H), 8.71 (d, J=8.3 Hz, 1H), 8.46 (s, 1H), 8.42 (s, 1H), 7.92 (s, 1H), 7.76 (d, J=8.7 Hz, 1H), 4.31 (s, 3H), 3.35 (s, 3H), 1.55 (s, 9H).

후처리

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in dichloromethane (0.7 ml)
  3. stirringThe reaction was stirred at room temperature for 1 h
  4. filtrationThe resulting suspension was filtered
  5. washwashed with hot water and ethyl acetate
  6. customThe product collected
  7. customwas dried under high vacuum

출처 및 근거

ORD 기록
ord-488edf4b3abf4e599a15bad42e248d8f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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