Trifluoroacetic acid → N-tert-butyl-2-(1,5-dimethyl-1H-pyrazol-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 522977ノート

反応式

HRID 522977 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][N:21]([CH3:24])[C:22]=3[CH3:23])[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:19]=[N:20][N:21]([CH3:24])[C:22]=3[CH3:23])[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 2

HCID 6422Trifluoroacetic acidHCID 90040996N-tert-butyl-2-(1,5-dimethyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

生成物 1

HCID 73295612N-tert-butyl-2-(1,5-dimethyl-1H-pyrazol-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide収率 56%

試薬・触媒・溶媒 3

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

実験手順

To a solution of N-tert-butyl-2-(1,5-dimethyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (45 mg, 98.3 μmol) in dichloromethane (1.5 mL) was added trifluoroacetic acid (224 mg, 152 μL, 1.97 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 (1.5 mL), methanol (0.75 mL) and ammonium hydroxide (0.2 mL) and stirred at room temperature for 2 h. The reaction mixture was concentrated then purified by chromatography (silica, 10-45% of a 1:4 methanol:dichloromethane solution in dichloromethane) to give N-tert-butyl-2-(1,5-dimethyl-1H-pyrazol-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (18 mg, 55.0 μmol, 56%) as a yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.10 (s, 1H), 8.39 (s, 1H), 7.87 (s, 1H), 7.86 (s, 1H), 7.85 (d, J=3.3, 1 H), 3.71 (s, 3H), 2.16 (s, 3H), 1.30 (s, 9H); MS (EI/CI) m/z: 328.2 [M+H].

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. stirringstirred at room temperature for 2 h
  4. concentrationThe reaction mixture was concentrated
  5. customthen purified by chromatography (silica, 10-45% of a 1:4 methanol:dichloromethane solution in dichloromethane)

出典と根拠

ORDレコード
ord-01d22eee68064624a1bb4fba234ec9f9
出典データセット
uspto-grants-2016_05
特許番号
US09334278B2

反応ノート

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