Trifluoroacetic acid → N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 522987

반응식

HRID 522987 반응식
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([N:17]([CH3:24])[C:18]3[CH:19]=[N:20][CH:21]=[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>ClCCl>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([N:17]([CH3:24])[C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=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 90041212N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

생성물 1

HCID 73295951N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide수율 59%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (38 mg, 83.6 μmol) was dissolved in dichloromethane (1.5 mL) and treated with trifluoroacetic acid (191 mg, 129 μL, 1.67 mmol). After 16 h, the mixture was concentrated and the residue re-dissolved in dichloromethane (1.5 mL), methanol (0.75 mL) and ammonium hydroxide (0.2 mL) and the mixture stirred at room temperature for 1 h. The mixture was concentrated then triturated with water and filtered to obtain a solid. This was washed with ether then dried to give N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (16 mg, 49.3 μmol, 59%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.33 (s, 1H), 8.64 (d, J=2.5, 1 H), 8.40 (dd, J=4.7, 1.2, 1 H), 8.05 (d, J=3.1, 1 H), 7.96 (s, 1H), 7.92 (s, 1H), 7.82 (m, 1H), 7.46 (m, 1H), 3.50 (s, 3H), 1.32 (s, 9H); MS (EI/CI) m/z: 325.1 [M+H].

후처리

  1. concentrationthe mixture was concentrated
  2. dissolutionthe residue re-dissolved in dichloromethane (1.5 mL)
  3. concentrationThe mixture was concentrated
  4. customthen triturated with water
  5. filtrationfiltered
  6. customto obtain a solid
  7. washThis was washed with ether
  8. customthen dried

출처 및 근거

ORD 기록
ord-30a7237b828a4d21aef5c77f1fb6d6cb
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334278B2

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