3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → N-(2-Methyl-2-(3-phenyl-1H-1,2,4-triazol-5-yl)propyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide

HRID 1397325Notes

Reaction equation

HRID 1397325 reaction equation
[CH3:1][C:2]([C:6]1[NH:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]=1)([CH3:5])[CH2:3][NH2:4].[F:17][C:18]([F:34])([F:33])[C:19]1[O:23][N:22]=[C:21]([C:24]2[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=2)[C:27](O)=[O:28])[N:20]=1>>[CH3:5][C:2]([C:6]1[NH:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]=1)([CH3:1])[CH2:3][NH:4][C:27](=[O:28])[C:26]1[CH:30]=[CH:31][CH:32]=[C:24]([C:21]2[N:20]=[C:19]([C:18]([F:34])([F:33])[F:17])[O:23][N:22]=2)[CH:25]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 673242222-methyl-2-(3-phenyl-1H-1,2,4-triazol-5-yl)propan-1-amine

Product 1

HCID 67325648N-(2-Methyl-2-(3-phenyl-1H-1,2,4-triazol-5-yl)propyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamideYield 25%

Procedure

This compound was synthesized from 2-methyl-2-(3-phenyl-1H-1,2,4-triazol-5-yl)propan-1-amine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (35 mg, yield 25%). 1H NMR (400 MHz, MeOD) δ 8.55 (s, 1H), 8.29-8.27 (d, J=7.8 Hz, 1H), 8.06-7.97 (m, 3H), 7.71-7.67 (t, J=8.7 Hz, 1H), 7.50-7.41 (m, 3H), 3.75 (s, 2H), 1.54-1.51 (m, 6H). MS (ESI) m/z: Calculated for C22H19F3N6O2: 456.15. found: 457.2 (M+H)+.

Sources & evidence

ORD record
ord-44dd1d910c484836adaa64c9cf09ff86
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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