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Dimethylformamide → 5-(1,2,4-triazol-4-yl)-1H-pyrrolo[2,3-c]pyridine

HRID 2393444
ノート
印刷プレビュー

反応式

HRID 2393444 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[CH:6][N:7]=1.[CH:11]([NH:13][NH:14][CH:15]=O)=O.CN(C=O)C.C(OCC)(=O)C>O>[N:13]1[N:14]=[CH:15][N:1]([C:2]2[CH:3]=[C:4]3[CH:10]=[CH:9][NH:8][C:5]3=[CH:6][N:7]=2)[CH:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 123421,2-HydrazinedicarboxaldehydeHCID 189753231H-Pyrrolo(2,3-c)pyridin-5-amine

生成物 1

HCID 189753585-(1,2,4-triazol-4-yl)-1H-pyrrolo[2,3-c]pyridine収率 59.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

5-Amino-1H-pyrrolo[2,3-c]pyridine (2 g, 15 mmol), diformylhydrazine (1.32 g, 15 mmol) and dry DMF (1.5 mL) were heated at 170° C. under nitrogen for 4 hours. After cooling, ethyl acetate (10 mL) and water (10 mL) were added. The mixture was stirred vigorously for 15 min. The resulting precipitate was collected by filtration, and chromatographed on silica eluting with a gradient of 5 to 7 to 10% MeOH in DCM to give a yellow solid. This was triturated with ether to give the title compound (1.65 g, 59%) as a yellow/green crystalline solid. mp 254°-257° C. 1H NMR (360 MHz, d6 -DMSO) δ 6.63 (1H, d, J=3.1Hz), 7.79 (1H, d, J=3.0Hz), 7.99 (1H, s), 8.71 (1H, s), 9.21 (2H, s) and 11.89 (1H, br s).

後処理

  1. temperatureAfter cooling
  2. filtrationThe resulting precipitate was collected by filtration
  3. customchromatographed on silica eluting with a gradient of 5 to 7 to 10% MeOH in DCM
  4. customto give a yellow solid
  5. customThis was triturated with ether

出典と根拠

ORDレコード
ord-a30dca9131174ecda669761d0526660f
出典データセット
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05807857

反応ノート

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