Ethylenediamine → 2-(1-methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

HRID 246291

反応式

HRID 246291 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:21]4=[N:22][CH:23]=[CH:24][CH:25]=[C:20]4[N:19]([CH3:26])[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>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:21]4=[N:22][CH:23]=[CH:24][CH:25]=[C:20]4[N:19]([CH3:26])[N:18]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 712796112-(1-methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

生成物 1

HCID 712800532-(1-methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide収率 64.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a 10 ml round-bottomed flask, 2-(1-methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (49 mg, 0.102 mmol) was dissolved in dichloromethane (0.6 ml) and trifluoroacetic acid (0.32 ml, 4.15 mmol) was added. The yellow reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was dissolved in dichloromethane (0.6 ml) and ethylenediamine (0.42 ml, 6.22 mmol) was added. The yellow solution was stirred at room temperature for 1 h then quenched with water and diluted with ethyl acetate. The resulting suspension was filtered and washed with hot water and ethyl acetate and the product dried under high vacuum to provide 23 mg (64%) of 2-(1-methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a light yellow powder. MS: (M+H)+=350; 1H NMR (DMSO-d6, 400 MHz): δ (ppm) 12.58 (br. s., 1H), 9.34 (s, 1H), 8.69 (s, 1H), 8.65 (dd, J=4.3, 1.3 Hz, 1H), 8.34 (s, 1H), 8.27 (dd, J=8.6, 1.3 Hz, 1H), 7.52 (dd, J=8.6, 4.3 Hz, 1H), 4.21 (s, 3H), 1.53 (s, 9H).

後処理

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in dichloromethane (0.6 ml)
  3. stirringThe yellow solution was stirred at room temperature for 1 h
  4. customthen quenched with water
  5. additiondiluted with ethyl acetate
  6. filtrationThe resulting suspension was filtered
  7. washwashed with hot water and ethyl acetate
  8. customthe product dried under high vacuum

出典と根拠

ORDレコード
ord-9331afedbe3a46b1a21f3627697775f0
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

関連ノート

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