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Ethylenediamine → 2-(6-fluoro-1-piperidin-4-yl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

HRID 246287
ノート
印刷プレビュー

反応式

HRID 246287 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]([F:26])=[CH:23][CH:24]=4)[N:19]([CH:27]4[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]4)[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:25]4[C:20](=[CH:21][C:22]([F:26])=[CH:23][CH:24]=4)[N:19]([CH:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)[N:18]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 712800342-[1-(1-tert-butoxycarbonyl-piperidin-4-yl)-6-fluoro-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

生成物 1

HCID 712800672-(6-fluoro-1-piperidin-4-yl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide収率 89.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a 10 ml round-bottomed flask, 2-[1-(1-tert-butoxycarbonyl-piperidin-4-yl)-6-fluoro-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (46 mg, 0.069 mmol) was dissolved in dichloromethane (0.4 ml) and trifluoroacetic acid (0.22 ml, 2.86 mmol) was added. The reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was suspended in dichloromethane (0.4 ml) and ethylenediamine (0.28 ml, 4.15 mmol) was added. The light yellow suspension was stirred at room temperature for 1 h then quenched with water and diluted with ethyl acetate. The suspension was filtered and washed with hot water and ethyl acetate then dried under high vacuum to provide 27 mg (85%) of 2-(6-fluoro-1-piperidin-4-yl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a light yellow powder. MS: (M+H)+=436; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 9.08 (s, 1H), 8.47 (dd, J=8.9, 5.5 Hz, 1H), 8.39 (s, 1H), 7.96 (s, 1H), 7.77-7.85 (m, 1H), 7.10-7.22 (m, 1H), 4.70-4.88 (m, 1H), 3.13 (d, J=12.1 Hz, 2H), 2.67-2.81 (m, 2H), 2.01-2.20 (m, 2H), 1.88-2.01 (m, 2H), 1.52 (s, 9H).

後処理

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

出典と根拠

ORDレコード
ord-6358ec004d0e4dddbb8b4b12be3425b2
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08658646B2

反応ノート

読み込み中…

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