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Trifluoroacetic acid → N-tert-butyl-2-(3-(methylsulfonyl)phenylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 522971
ノート
印刷プレビュー

反応式

HRID 522971 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:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=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>ClCCl.CO.[OH-].[NH4+]>[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:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 6422Trifluoroacetic acidHCID 131735556N-tert-butyl-2-(3-(methylsulfonyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

生成物 1

HCID 73295275N-tert-butyl-2-(3-(methylsulfonyl)phenylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide収率 57%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒
HCID 6344
Dichloromethane
溶媒
2 回
HCID 14923Ammonium Hydroxide溶媒

実験手順

To a solution of N-tert-butyl-2-(3-(methylsulfonyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (61 mg, 118 mol) in dichloromethane (1.8 mL) was added trifluoroacetic acid (269 mg, 182 μL, 2.36 mmol) and the mixture stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo and the residue obtained diluted with dichloromethane (1.8 mL), methanol (0.9 mL) and ammonium hydroxide (0.25 mL) and stirred at room temperature for 1 h. The mixture was concentrated and triturated with water. The solid was collected by filtration and washed with water and ether. Purification by chromatography (silica, GRADIENT UNKNOWN dichloromethane/methanol/0.5% ammonium hydroxide) gave N-tert-butyl-2-(3-(methylsulfonyl)phenylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (26 mg, 67.1 mol, 57%) as a yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.42 (s, 1H), 9.87 (s, 1H), 8.33 (d, J=8.2, 1 H), 8.05 (d, J=3.4, 1 H), 8.03 (s, 1H), 7.79 (t, J=2.0, 1 H), 7.68 (s, 1H), 7.54 (t, J=8.0, 1 H), 7.47 (d, J=7.7, 1 H), 3.21 (s, 3H), 1.42 (s, 9H); MS (EI/CI) m/z: 388.2 [M+H].

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. stirringstirred at room temperature for 1 h
  4. concentrationThe mixture was concentrated
  5. customtriturated with water
  6. filtrationThe solid was collected by filtration
  7. washwashed with water and ether
  8. customPurification by chromatography (silica, GRADIENT UNKNOWN dichloromethane/methanol/0.5% ammonium hydroxide)

出典と根拠

ORDレコード
ord-689aa6b7278440bdb98555d9fc399094
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09334278B2

反応ノート

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