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

HRID 59520Notes

Reaction equation

HRID 59520 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]([F:38])=[CH:28][C:29]([Cl:37])=[C:30]([CH:36]=1)[C:31]([N:33]=[C:34]=[O:35])=O)=[O:23].FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:37][C:29]1[C:30]([C:31]2[NH:33][C:34](=[O:35])[N:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:19])[F:18])=[CH:4][CH:5]=3)[N:10]=2)=[CH:36][C:26]([CH2:25][NH:24][C:22](=[O:23])[C:21]([F:40])([F:39])[F:20])=[C:27]([F:38])[CH:28]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 900189655-((2,2,2-Tri fluoroacetamido)methyl)-2-chloro-4-fluorobenzoyl isocyanateHCID 90019516tert-Butyl 2-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate

Product 1

HCID 136246098N-(4-chloro-2-fluoro-5-(1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)benzyl)-2,2,2-trifluoroacetamideYield 6.7%

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, 0.300 g), 5-((2,2,2-trifluoroacetamido)methyl)-2-chloro-4-fluorobenzoyl isocyanate (Intermediate-69, 0.300 g), DCM (20 mL), trifluoro acetic acid (5.0 mL) to afford 0.030 g of the desired product. 1H NMR (400 MHz, DMSO d6): δ 4.49 (m, 2H), 7.74-7.77 (m, 1H), 7.78-7.80 (m, 1H), 7.87 (d, J=5.1 Hz, 2H), 8.19 (d, J=4.2 Hz, 2H), 10.06 (m, 1H), 12.76 (s, 1H); MS (m/z): 467.15 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-a77ce3fa5b674c5499ef83894768bfed
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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