Trifluoroacetic acid → 6-(Difluoromethyl)-5-(5-oxo-1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)nicotinonitrile

HRID 59565Notes

Reaction equation

HRID 59565 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]([CH:14]([F:16])[F:15])=[C:7]([CH:13]=1)[C:8]([N:10]=[C:11]=[O:12])=O)#[N:2].[F:17][C:18]([F:35])([F:34])[C:19]1[CH:24]=[CH:23][C:22]([NH:25][NH:26]C(OC(C)(C)C)=O)=[CH:21][CH:20]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:15][CH:14]([F:16])[C:6]1[C:7]([C:8]2[NH:10][C:11](=[O:12])[N:25]([C:22]3[CH:23]=[CH:24][C:19]([C:18]([F:17])([F:35])[F:34])=[CH:20][CH:21]=3)[N:26]=2)=[CH:13][C:3]([C:1]#[N:2])=[CH:4][N:5]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 900192245-Cyano-2-(difluoromethyl)nicotinoyl isocyanateHCID 90019516tert-Butyl 2-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate

Product 1

HCID 1364923766-(Difluoromethyl)-5-(5-oxo-1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)nicotinonitrileYield 22.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by following the procedure as described in Example-83 by using 5-cyano-2-(difluoromethyl)nicotinoyl isocyanate (Intermediate-145, 0.900 g, 4.03 mmol), tert-butyl 2-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate (Intermediate-53, 1.0 g, 163 mmol), TFA (10 mL), DCM (40 mL) to afford 0.350 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 7.45-7.56 (t, J=53.4 Hz, 1H), 7.90 (d, J=9.3 Hz, 2H), 8.20 (d, J=8.7 Hz, 2H), 8.77 (s, 1H), 9.32 (s, 1H), 13.01 (s, 1H); MS (m/z): 382.15 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-d4436a58d46544d0b1bab30791c29e75
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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