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

HRID 508997Notes

Reaction equation

HRID 508997 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])=[CH:4][C:3]=1[NH:15][NH:16]C(OC(C)(C)C)=O.[F:24][C:25]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:26]=1[C:27]([N:29]=[C:30]=[O:31])=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])=[CH:4][C:3]=1[N:15]1[C:30](=[O:31])[NH:29][C:27]([C:26]2[CH:32]=[CH:33][C:34]([C:36]([F:39])([F:38])[F:37])=[CH:35][C:25]=2[F:24])=[N:16]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 90019289Tert-butyl 2-(2-chloro-5-(cyclopropanecarboxamidomethyl) phenyl)hydrazinecarboxylateHCID 900197172-Fluoro-4-(trifluoromethyl)benzoyl isocyanate

Product 1

HCID 136246023N-(4-Chloro-3-(3-(2-fluoro-4-(trifluoromethyl)phenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)benzyl)cyclopropanecarboxamideYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by following the procedure as described for Example-83 by using tert-butyl 2-(2-chloro-5-(cyclopropanecarboxamidomethyl)phenyl)hydrazinecarboxylate (step-7 of Intermediate-48, 0.060 g, 0.17 mmol), 2-fluoro-4-(trifluoromethyl)benzoyl isocyanate (Intermediate-56, 0.035 g, 0.82 mmol), DCM (10 mL) and TFA (3 mL) to afford 0.045 g of desired product. 1H NMR (400 MHz, DMSO d6): δ 0.67 (m, 4H), 1.60 (m, 1H), 4.3 (d, J=5.9 Hz, 2H), 7.37 (d, J=6.4 Hz, 1H), 7.46 (s, 1H), 7.60 (d, J=8.3 Hz, 1H), 7.74 (d, J=8.2 Hz, 1H), 7.89 (d, J=10.56 Hz, 1H), 8.05 (t, J=7.7 Hz, 1H), 8.65 (t, J=5.8 Hz, 1H), 12.6 (br s, 1H); MS (m/z): 454.98 (M+).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-387880c0604d4408b698e3ab167c7632
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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