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

HRID 59523Notes

Reaction equation

HRID 59523 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH:9]C(OC(C)(C)C)=O)=[CH:4][C:3]=1[F:17].[Cl:18][C:19]1[CH:29]=[CH:28][C:27]([CH2:30][NH:31][C:32](=[O:37])[C:33]([F:36])([F:35])[F:34])=[CH:26][C:20]=1[C:21]([N:23]=[C:24]=[O:25])=O.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:18][C:19]1[CH:29]=[CH:28][C:27]([CH2:30][NH:31][C:32](=[O:37])[C:33]([F:36])([F:35])[F:34])=[CH:26][C:20]=1[C:21]1[NH:23][C:24](=[O:25])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([F:17])[CH:4]=2)[N:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 900192862-Chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoyl isocyanateHCID 90065779tert-Butyl 2-(4-chloro-3-fluorophenyl)hydrazinecarboxylate

Product 1

HCID 136246047N-(4-chloro-3-(1-(4-chloro-3-fluorophenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)benzyl)-2,2,2-trifluoroacetamideYield 37,104.102%

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-chloro-3-fluorophenyl)hydrazinecarboxylate (Intermediate-71, 0.828 g, 0.003 mmol), 2-chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoyl isocyanate (step-3 of Intermediate-26, 1.3 g, 0.043 mmol), DCM (20 mL), trifluoro acetic acid (5.0 mL) to afford 0.500 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 4.45 (d, 2H), 7.48 (d, J=15.0 Hz, 1H), 7.68-7.83 (m, 3H), 7.85 (d, 1H), 7.99 (d, J=17.1 Hz, 1H), 10.08 (d, J=12.0 Hz, 1H), 12.73 (s, 1H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-8aedc481a0214e938872d14038c28027
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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