2-(3-(4-fluorophenyl)-1H-1,2,4-triazol-5-yl)-2-methylpropan-1-amine → N-(2-(3-(4-Fluorophenyl)-1H-1,2,4-triazol-5-yl)-2-methylpropyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide

HRID 1397328Notes

Reaction equation

HRID 1397328 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]([CH3:17])([CH3:16])[CH2:14][NH2:15])[NH:10][N:9]=2)=[CH:4][CH:3]=1.[F:18][C:19]([F:35])([F:34])[C:20]1[O:24][N:23]=[C:22]([C:25]2[CH:26]=[N:27][CH:28]=[C:29]([CH:33]=2)[C:30](O)=[O:31])[N:21]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([C:13]([CH3:17])([CH3:16])[CH2:14][NH:15][C:30](=[O:31])[C:29]3[CH:33]=[C:25]([C:22]4[N:21]=[C:20]([C:19]([F:35])([F:34])[F:18])[O:24][N:23]=4)[CH:26]=[N:27][CH:28]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 673237882-(3-(4-fluorophenyl)-1H-1,2,4-triazol-5-yl)-2-methylpropan-1-amineHCID 673242165-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid

Product 1

HCID 69949950N-(2-(3-(4-Fluorophenyl)-1H-1,2,4-triazol-5-yl)-2-methylpropyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamideYield 11%

Procedure

This compound was synthesized from 2-(3-(4-fluorophenyl)-1H-1,2,4-triazol-5-yl)-2-methylpropan-1-amine and 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid as described in example 8 step 6 (20 mg, yield 11%). 1H NMR (400 MHz, MeOD) δ 9.38-9.37 (d, J=1.5 Hz, 1H), 9.15 (d, J=1.5 Hz, 1H), 8.82 (m, 1H), 8.06-8.02 (m, 2H), 7.21-7.17 (t, J=8.5 Hz, 2H), 3.76 (s, 2H), 1.53 (s, 6H). MS (ESI) m/z: Calculated for C21H17F4N7O2: 475.14. found: 476.2 (M+H)+.

Sources & evidence

ORD record
ord-cc42565a12034e7885223ad224e34845
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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