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

HRID 246295

반응식

HRID 246295 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]([C:26]#[N:27])[CH:24]=4)[N:19]([CH3:28])[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][CH:22]=[C:23]([C:26]#[N:27])[CH:24]=4)[N:19]([CH3:28])[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 712803922-(5-cyano-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

생성물 1

HCID 712804332-(5-cyano-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide수율 73%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

In a round-bottomed flask, 2-(5-cyano-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (80 mg, 0.16 mmol) was dissolved in dichloromethane (0.8 ml) and trifluoroacetic acid (0.5 ml, 6.4 mmol) was added. The reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was suspended in dichloromethane (0.8 ml) and ethylenediamine (0.65 ml, 9.63 mmol) was added. The light yellow suspension was stirred at room temperature for 1 h then water and ethyl acetate were added. The suspension was filtered and washed with hot water and ethyl acetate. The product collected was dried under high vacuum to provide 43 mg (73%) of 2-(5-cyano-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a yellow powder. MS: (M+Na)+=396; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 12.48 (br. s., 1H), 9.10 (s, 1H), 8.87 (s, 1H), 8.41 (s, 1H), 7.93-8.05 (m, 1H), 7.78-7.90 (m, 2H), 4.23 (s, 3H), 1.54 (s, 9H).

후처리

  1. concentrationthen concentrated
  2. stirringThe light yellow suspension was stirred at room temperature for 1 h
  3. filtrationThe suspension was filtered
  4. washwashed with hot water and ethyl acetate
  5. customThe product collected
  6. customwas dried under high vacuum

출처 및 근거

ORD 기록
ord-38240a3ce6c34b9bb5a5e9bd8e1815e0
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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