N,N-Dimethyl-2-(2-acetylamino-5-nitropyridin-4-yl)ethenamine → N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamide

HRID 2393442노트

반응식

HRID 2393442 반응식
CN(C)[CH:3]=[CH:4][C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][N:8]=[C:7]([NH:14][C:15](=[O:17])[CH3:16])[CH:6]=1.[H][H]>C(O)C.[Pt]=O>[C:15]([NH:14][C:7]1[CH:6]=[C:5]2[CH:4]=[CH:3][NH:11][C:10]2=[CH:9][N:8]=1)(=[O:17])[CH3:16]

참가 물질

5

반응물 2

HCID 53811652N,N-Dimethyl-2-(2-acetylamino-5-nitropyridin-4-yl)ethenamineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 18975304N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamide수율 33.3%

시약·촉매·용매 2

HCID 82844Platinum oxide (PtO)촉매HCID 702Ethanol용매

실험 절차

N,N-Dimethyl-2-(2-acetylamino-5-nitropyridin-4-yl)ethenamine (6 g, 24 mmol) was hydrogenated over platinum oxide (0.5 g) in ethanol (120 mL) at 35 psi of hydrogen for 15 min. The catalyst was removed by filtration and the solvent evaporated in vacuo. The residue was chromatographed on silica eluting with a gradient of 5 to 10% MeOH in DCM to afford a purple solid. This was triturated with ether and the precipitate collected by filtration to give the title compound (1.4 g, 33%) as a beige solid. mp 220° C. (dec.). 1H NMR (360 MHz, d6 -DMSO) δ 2.07 (3H, s), 6.45 (1H, s), 7.55-7.57 (1H, m), 8.21 (1H, s), 8.46 (1H, s), 10.16 (1H, br s) and 11.42 (1H, br s).

후처리

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated in vacuo
  3. customThe residue was chromatographed on silica eluting with a gradient of 5 to 10% MeOH in DCM
  4. customto afford a purple solid
  5. customThis was triturated with ether
  6. filtrationthe precipitate collected by filtration

출처 및 근거

ORD 기록
ord-928529796528427aa2e02af5cdff0ed9
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05807857

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