Trifluoroacetic acid → N-(3-(1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-2,4-dimethylbenzyl)-2,2,2-trifluoro acetamide

HRID 59513Notes

Reaction equation

HRID 59513 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10]C(OC(C)(C)C)=O)=[CH:5][CH:4]=1.[F:20][C:21]([F:40])([F:39])[C:22]([NH:24][CH2:25][C:26]1[C:27]([CH3:38])=[C:28]([C:34]([CH3:37])=[CH:35][CH:36]=1)[C:29]([N:31]=[C:32]=[O:33])=O)=[O:23].FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]([F:18])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:32](=[O:33])[NH:31][C:29]([C:28]3[C:27]([CH3:38])=[C:26]([CH:36]=[CH:35][C:34]=3[CH3:37])[CH2:25][NH:24][C:22](=[O:23])[C:21]([F:40])([F:39])[F:20])=[N:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 900192983-((2,2,2-Trifluoroacetamido)methyl)-2,6-dimethylbenzoyl isocyanateHCID 90019516tert-Butyl 2-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate

Product 1

HCID 136246060N-(3-(1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-2,4-dimethylbenzyl)-2,2,2-trifluoro acetamideYield 45.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example-83 by using tert-butyl 2-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate (Intermediate-53, 1.00 g, 3.63 mmol), 3-((2,2,2-trifluoroacetamido)methyl)-2,6-dimethylbenzoyl isocyanate (Intermediate-65, 1.00 g, 3.33 mmol), DCM (20 mL), trifluoro acetic acid (5.0 mL) to afford 0.700 g of the desired product. 1H NMR (400 MHz, DMSO d6): δ 2.20 (s, 3H), 2.22 (s, 3H), 4.40 (d, J=4.2 Hz, 2H), 7.21 (d, J=6.0 Hz, 1H), 7.29 (d, J=6.0 Hz, 1H), 7.82 (d, J=6.6 Hz, 1H), 8.17 (d, J=6.6 Hz, 1H), 9.95 (t, J=6.9 Hz, 1H), 12.32 (br s, 1H); MS (m/z): 457.26 (M−H)−.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-eeae59b62e3e4567b42c70809c8d200f
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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