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

HRID 2393444
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HRID 2393444 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a30dca9131174ecda669761d0526660f
출처 데이터셋
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05807857

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