HCID 69932754, compound → HCID 53250653, compound

HRID 509623Notes

Reaction equation

HRID 509623 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:7]=[C:8](/[CH:12]=[CH:13]/[C:14]3[N:24]=[C:17]4[C:18]([CH3:23])=[N:19][CH:20]=[C:21]([CH3:22])[N:16]4[N:15]=3)[N:9]([CH3:11])[CH:10]=2)=[CH:2]1>CN(C=O)C>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:7]=[C:8]([CH2:12][CH2:13][C:14]3[N:24]=[C:17]4[C:18]([CH3:23])=[N:19][CH:20]=[C:21]([CH3:22])[N:16]4[N:15]=3)[N:9]([CH3:11])[CH:10]=2)=[CH:2]1

Participants

3

Reactant 1

HCID 69932754HCID 69932754, compound

Product 1

HCID 53250653HCID 53250653, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-[(E)-2-(4-Furan-3-yl-1-methyl-1H-imidazol-2-yl)-vinyl]-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (170 mg, 0.53 mmol) in DMF (13 mL) was added p-toluenesulfonylhydrazide (300 mg, 1.6 mmol). The reaction was stirred for 8 hours at 120° C. The volatiles were removed in vacuo and the residue dissolved in EtOAc (50 mL), washed with saturated sodium bicarbonate solution, brine solution and dried (MgSO4). Filtration, evaporation of the volatiles and purification by column chromatography on silica gel (EtOAc 100%) afforded the title compound (126 mg, 74%). LC-MS: m/z=323.3 (MH+), tR=0.48 minutes, method C.

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue dissolved in EtOAc (50 mL)
  3. washwashed with saturated sodium bicarbonate solution, brine solution
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration, evaporation of the volatiles and purification by column chromatography on silica gel (EtOAc 100%)

Sources & evidence

ORD record
ord-14af1bcfd91b43fe9dea96861bfea8d0
Source dataset
uspto-grants-2015_08
Patent number
US09096589B2

Reaction notes

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