Methanol → N-tert-butyl-2-(6-methylpyridin-3-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 522957

反応式

HRID 522957 の反応式
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([NH:17][C:18]3[CH:19]=[N:20][C:21]([CH3:24])=[CH:22][CH:23]=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.CO.[OH-].[NH4+]>ClCCl>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([NH:17][C:18]3[CH:19]=[N:20][C:21]([CH3:24])=[CH:22][CH:23]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 131735549N-tert-butyl-2-(6-methylpyridin-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

生成物 1

HCID 73295609N-tert-butyl-2-(6-methylpyridin-3-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide収率 84.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of N-tert-butyl-2-(6-methylpyridin-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (55 mg, 121 mol) in dichloromethane (1.9 mL) was added trifluoroacetic acid (276 mg, 186 μL, 2.42 mmol) and the mixture stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo and the residue obtained then dissolved in dichloromethane (2 mL), methanol (1 mL) and ammonium hydroxide (0.25 mL) and the mixture stirred at room temperature for 1 h. The mixture was concentrated and triturated with water, then filtered to obtain a solid which was washed with ether and dried to give N-tert-butyl-2-(6-methylpyridin-3-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (33 mg, 102 mol, 84%) as a brown solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.23 (s, 1H), 9.41 (s, 1H), 8.60 (d, J=2.3, 1 H), 7.91 (m, 3H), 7.59 (s, 1H), 7.06 (d, J=8.5, 1 H), 2.31 (s, 3H), 1.32 (s, 9H); MS (EI/CI) m/z: 325.1 [M+H].

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. concentrationThe mixture was concentrated
  4. customtriturated with water
  5. filtrationfiltered
  6. customto obtain a solid which
  7. washwas washed with ether
  8. customdried

出典と根拠

ORDレコード
ord-4b7a83fa5a344ddea4cb9b7c6ed63fa3
出典データセット
uspto-grants-2016_05
特許番号
US09334278B2

関連ノート

読み込み中…