Trifluoroacetic acid → N-(4-chloro-3-(1-(3-(trifluoromethyl)phenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)benzyl)-2,2,2-trifluoroacetamide

HRID 59400Notes

Reaction equation

HRID 59400 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])=[CH:9][C:3]=1[C:4]([N:6]=[C:7]=[O:8])=O.[F:21][C:22]([F:39])([F:38])[C:23]1[CH:24]=[C:25]([NH:29][NH:30]C(OC(C)(C)C)=O)[CH:26]=[CH:27][CH:28]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])=[CH:9][C:3]=1[C:4]1[NH:6][C:7](=[O:8])[N:29]([C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([C:22]([F:21])([F:39])[F:38])[CH:24]=2)[N:30]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 900192862-Chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoyl isocyanateHCID 90019526Tert-butyl 2-[3-(trifluoromethyl)phenyl]hydrazinecarboxylate

Product 1

HCID 136492416N-(4-chloro-3-(1-(3-(trifluoromethyl)phenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)benzyl)-2,2,2-trifluoroacetamideYield 55.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example-83 by using 2-chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoyl isocyanate (step-3 of Intermediate-26, 0.500 g, 1.55 mmol), tert-butyl 2-[3-(trifluoromethyl)phenyl]hydrazinecarboxylate (0.428 g, 1.55 mmol), DCM (20 mL) and trifluoro acetic acid (5.0 mL) to afford 0.400 g of the desired product.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-a767fa143feb47579ed2869b31ff48a0
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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