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

HRID 522955노트

반응식

HRID 522955 반응식
[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]([CH3:23])[CH:22]=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>[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]([CH3:23])[CH:22]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 131735548N-tert-butyl-2-(1-methyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

생성물 1

HCID 73295610N-tert-butyl-2-(1-methyl-1H-pyrazol-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide수율 92%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of N-tert-butyl-2-(1-methyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (89 mg, 201 mol) in dichloromethane (3 mL) was added trifluoroacetic acid (458 mg, 309 μL, 4.01 mmol) and the reaction mixture stirred at room temperature for 16 h. The mixture was concentrated in vacuo then dissolved in dichloromethane (3 mL), methanol (1.5 mL) and ammonium hydroxide (0.45 mL) and the mixture stirred at room temperature for 1 h. After concentration in vacuo, the mixture was triturated with water and filtered to collect the solid. The solid was washed with ether and dried to give N-tert-butyl-2-(1-methyl-1H-pyrazol-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (58 mg, 185 mol, 92%) as a brown solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.18 (s, 1H), 9.11 (s, 1H), 7.90 (d, J=3.2, 1 H), 7.86 (s, 1H), 7.85 (s, 1H), 7.72 (s, 1H), 7.55 (s, 1H), 3.80 (s, 3H), 1.43 (s, 9H); MS (EI/CI) m/z: 314.1 [M+H].

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthen dissolved in dichloromethane (3 mL)
  3. stirringmethanol (1.5 mL) and ammonium hydroxide (0.45 mL) and the mixture stirred at room temperature for 1 h
  4. concentrationAfter concentration in vacuo
  5. customthe mixture was triturated with water
  6. filtrationfiltered
  7. customto collect the solid
  8. washThe solid was washed with ether
  9. customdried

출처 및 근거

ORD 기록
ord-cff5a9113eb6465187d5e13c9861e1a9
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334278B2

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