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

HRID 246327ノート

反応式

HRID 246327 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-488edf4b3abf4e599a15bad42e248d8f
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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