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

HRID 59372Notes

Reaction equation

HRID 59372 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([NH:5][CH2:6][C:7]1[C:8]([O:19][CH3:20])=[CH:9][C:10]([Cl:18])=[C:11]([CH:17]=1)[C:12]([N:14]=[C:15]=[O:16])=O)=[O:4].[F:23][C:24]([F:41])([F:40])[C:25]1[CH:30]=[CH:29][C:28]([NH:31][NH:32]C(OC(C)(C)C)=O)=[CH:27][CH:26]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:18][C:10]1[C:11]([C:12]2[NH:14][C:15](=[O:16])[N:31]([C:28]3[CH:29]=[CH:30][C:25]([C:24]([F:23])([F:41])[F:40])=[CH:26][CH:27]=3)[N:32]=2)=[CH:17][C:7]([CH2:6][NH:5][C:3](=[O:4])[C:2]([F:22])([F:21])[F:1])=[C:8]([O:19][CH3:20])[CH:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 90019516tert-Butyl 2-(4-(trifluoromethyl)phenyl)hydrazinecarboxylateHCID 900198525-((2,2,2-Trifluoroacetamido)methyl)-2-chloro-4-methoxybenzoyl isocyanate

Product 1

HCID 136492372N-(4-chloro-5-(1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-2-methoxybenzyl)-2,2,2-trifluoroacetamideYield 24.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example-83 by using 5-((2,2,2-trifluoroacetamido)methyl)-2-chloro-4-methoxybenzoyl isocyanate (0.500 g), tert-butyl 2-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate (Intermediate-53, 0.450 g), DCM (20 mL), and trifluoro acetic acid (5.0 mL) to afford 0.180 g of the desired product.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-d53ecee8b98a4759aa7ea3b93503a5c6
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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