HCID 53251154, compound → HCID 53251156, compound

HRID 1627740Notes

Reaction equation

HRID 1627740 reaction equation
[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][CH2:12][C:13]3[N:17]([CH2:18][CH2:19][C:20]#[N:21])[N:16]=[C:15]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:14]=3)[N:10]=[C:6]2[C:5]([CH3:28])=[N:4][CH:3]=1>N.CO.[Ni]>[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][CH2:12][C:13]3[N:17]([CH2:18][CH2:19][CH2:20][NH2:21])[N:16]=[C:15]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:14]=3)[N:10]=[C:6]2[C:5]([CH3:28])=[N:4][CH:3]=1

Participants

5

Reactant 1

HCID 53251154HCID 53251154, compound

Product 1

HCID 53251156HCID 53251156, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

3-{5-[2-(5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-ethyl]-3-phenyl-1,2,4-triazol-1-yl}-propionitrile (28 mg, 0.075 mmol) was dissolved in 2 M of Ammonia in Methanol (15 mL) and hydrogenated on an H-cube through a column of Raney-Nickel (50 bar hydrogen, rt). The solvent was evaporated off. The crude product was purified by silica gel chromatography (Eluent: 10% MeOH, 10% triethylamine, 80% EtOAc). Yield: 10 mg (35%) of the title compound as a clear oil. LC-MS: m/z=377.3 (MH+), tR=0.81 min, Method C.

Workup

  1. customThe solvent was evaporated off
  2. customThe crude product was purified by silica gel chromatography (Eluent: 10% MeOH, 10% triethylamine, 80% EtOAc)

Sources & evidence

ORD record
ord-c07f92825c0644cea18b867830017b87
Source dataset
uspto-grants-2014_07
Patent number
US08785653B2

Reaction notes

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