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

HRID 522957

반응식

HRID 522957 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][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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-4b7a83fa5a344ddea4cb9b7c6ed63fa3
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334278B2

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