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

HRID 2393444Notes

Reaction equation

HRID 2393444 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a30dca9131174ecda669761d0526660f
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

Loading…