Trifluoroacetic acid → N-(3-(1-tert-butyl-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-4-chlorobenzyl)-2,2,2-trifluoroacetamide

HRID 59526Notes

Reaction equation

HRID 59526 reaction equation
[C:1]([NH:5][NH:6]C(OC(C)(C)C)=O)([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:25]=[CH:24][C:23]([CH2:26][NH:27][C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])=[CH:22][C:16]=1[C:17]([N:19]=[C:20]=[O:21])=O.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([N:5]1[C:20](=[O:21])[NH:19][C:17]([C:16]2[CH:22]=[C:23]([CH:24]=[CH:25][C:15]=2[Cl:14])[CH2:26][NH:27][C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 3771477N'-t-Butyl(tert-butoxy)carbohydrazideHCID 900192862-Chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoyl isocyanate

Product 1

HCID 136612564N-(3-(1-tert-butyl-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-4-chlorobenzyl)-2,2,2-trifluoroacetamideYield 22.1%

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-tert-butylhydrazinecarboxylate (Intermediate-74, 0.233 g, 1.2 mmol), 2-chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoyl isocyanate (step-3 of Intermediate-26, 0.400 g, 1.2 mmol), DCM (10 mL), trifluoro acetic acid (5.0 mL) to afford 0.100 g of the desired product. 1H NMR (400 MHz; DMSO d6): δ 1.52 (s, 9H), 4.42 (s, 2H), 7.39 (d, 1H), 7.41 (s, 1H), 7.58 (d, J=2.1 Hz, 2H), 10.0 (br s, 1H), 12.0 (br s, 1H); MS (in/z): 377.20 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-b4b6d64b6f3e4658b68c58927c09d915
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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