Trifluoroacetic acid → N-(4-Chloro-3-(4,5-dihydro-3-(4-(5-isopropyl-1,3,4-oxadiazol-2-yl)phenyl)-5-oxo-1,2,4-triazol-1-yl)benzyl)pivalamide

HRID 59558

Reaction equation

HRID 59558 reaction equation
[CH:1]([C:4]1[O:8][C:7]([C:9]2[CH:19]=[CH:18][C:12]([C:13]([N:15]=[C:16]=[O:17])=O)=[CH:11][CH:10]=2)=[N:6][N:5]=1)([CH3:3])[CH3:2].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:23][C:22]=1[NH:35][NH:36]C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:23][C:22]=1[N:35]1[C:16](=[O:17])[NH:15][C:13]([C:12]2[CH:18]=[CH:19][C:9]([C:7]3[O:8][C:4]([CH:1]([CH3:3])[CH3:2])=[N:5][N:6]=3)=[CH:10][CH:11]=2)=[N:36]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 90019804Tert-butyl 2-(2-chloro-5-(((2,2-dimethylpropanoyl)amino)methyl)phenyl)hydrazinecarboxylateHCID 900275314-(5-Isopropyl-1,3,4-oxadiazol-2-yl)benzoyl isocyanate

Product 1

HCID 136492567N-(4-Chloro-3-(4,5-dihydro-3-(4-(5-isopropyl-1,3,4-oxadiazol-2-yl)phenyl)-5-oxo-1,2,4-triazol-1-yl)benzyl)pivalamideYield 43.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example-83 by using 4-(5-isopropyl-1,3,4-oxadiazol-2-yl)benzoyl isocyanate (Intermediate-104, 0.196 g, 0.84 mmol), tert-butyl 2-(2-chloro-5-{[(2,2-dimethylpropanoyl)amino]methyl}phenyl)hydrazinecarboxylate (Intermediate-94, 0.150 g, 0.420 mmol), DCM (15 mL), and trifluoro acetic acid (3.0 mL) to afford 0.090 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 1.06 (s, 9H), 1.35 (s, 6H), 3.25 (m, 1H), 4.27 (d, J=5.4 Hz, 2H), 7.34 (d, J=8.1 Hz, 1H), 7.44 (s, 1H), 7.59 (d, J=8.4 Hz, 1H), 8.01-8.04 (m, 2H), 8.10-8.17 (m, 3H), 12.73 (s, 1H); MS (m/z): 495.39 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-6a0c82a143134ddf9d39ba714f88ef5a
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Linked notes

Loading…