Trifluoroacetic acid → N-(4-Chloro-3-(1-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-2-fluorobenzyl)pivalamide

HRID 59506Notes

Reaction equation

HRID 59506 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][CH:3]=1.[Cl:17][C:18]1[C:23]([C:24]([N:26]=[C:27]=[O:28])=O)=[C:22]([F:29])[C:21]([CH2:30][NH:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:20][CH:19]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:30][NH:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[C:22]([F:29])[C:23]=1[C:24]1[NH:26][C:27](=[O:28])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 59485730tert-Butyl 2-(4-chlorophenyl)hydrazinecarboxylateHCID 900197456-Chloro-2-fluoro-3-(pivalamidomethyl)benzoyl isocyanate

Product 1

HCID 136246037N-(4-Chloro-3-(1-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-2-fluorobenzyl)pivalamide

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-(4-chlorophenyl)hydrazinecarboxylate (Intermediate-62, 0.050 g, 0.20 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoyl isocyanate (Intermediate-51, 0.130 g, 0.41 mmol), DCM (10 mL) and TFA (3 mL) to afford 0.040 g of pure product. 1H NMR (400 MHz, DMSO d6): δ 1.12 (s, 9H), 4.30 (d, J=6.0 Hz, 2H), 7.24-7.47 (m, 2H), 7.52 (d, J=7.2 Hz, 2H), 7.94 (d, J=8.8 Hz, 2H), 8.16 (m, 1H), 12.10 (br s, 1H); MS (m/z): 437.16 (M+).

Sources & evidence

ORD record
ord-3c7ba59df43f4342a84e3847d29e3340
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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