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

HRID 1397326Notes

Reaction equation

HRID 1397326 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]=[N:26][CH:27]=[C:28]([CH:32]=2)[C:29](O)=[O:30])[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:29](=[O:30])[C:28]1[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]=[N:26][CH:27]=1

Participants

3

Reactant 2

HCID 673242165-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acidHCID 673242222-methyl-2-(3-phenyl-1H-1,2,4-triazol-5-yl)propan-1-amine

Product 1

HCID 69950156N-(2-Methyl-2-(3-phenyl-1H-1,2,4-triazol-5-yl)propyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamideYield 23%

Procedure

This compound was synthesized from 2-methyl-2-(3-phenyl-1H-1,2,4-triazol-5-yl)propan-1-amine and 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid as described in example 8 step 6 (20 mg, yield 23%). 1H NMR (400 MHz, MeOD) δ 9.37 (m, 1H), 9.16 (m, 1H), 8.84-8.13 (m, 1H), 8.02-7.99 (m, 2H), 7.48-7.42 (m, 3H), 3.77 (s, 2H), 1.54 (m, 6H). MS (ESI) m/z: Calculated for C21H18F3N7O2: 457.15. found: 458.2 (M+H)+.

Sources & evidence

ORD record
ord-3880b46648c44c80a5c6faf8a1304a31
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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