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

HRID 2393442ノート

反応式

HRID 2393442 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-928529796528427aa2e02af5cdff0ed9
出典データセット
uspto-grants-1998_09
特許番号
US05807857

反応ノート

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