6-(Difluoromethyl)-5-(5-oxo-1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)nicotinonitrile → 3-(5-(aminomethyl)-2-(difluoromethyl)pyridin-3-yl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-5(4H)-one

HRID 59568Notes

Reaction equation

HRID 59568 reaction equation
[F:1][CH:2]([F:27])[C:3]1[C:10]([C:11]2[NH:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[N:12]=2)=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1>C(O)C.[Ni]>[NH2:8][CH2:7][C:6]1[CH:9]=[C:10]([C:11]2[NH:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:26])[F:25])=[CH:19][CH:18]=3)[N:12]=2)[C:3]([CH:2]([F:27])[F:1])=[N:4][CH:5]=1

Participants

4

Reactant 1

HCID 1364923766-(Difluoromethyl)-5-(5-oxo-1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)nicotinonitrile

Product 1

HCID 1364923963-(5-(aminomethyl)-2-(difluoromethyl)pyridin-3-yl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-5(4H)-oneYield 998.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

The title compound was prepared according to the procedure described in Intermediate-16 by using 6-(difluoromethyl)-5-(5-oxo-1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)nicotinonitrile (Example-183, 0.050 g, 0.13 mmol), Raney Ni (catalytic amount), TEA (0.040 g, 0.39 mmol) in ethanol (20 mL) to afford 0.50 g of the desired product.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-cd01e0fad60242a7ae89135d8580fe9e
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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