3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → N-(2-(2-(4-chlorophenyl)thiazol-4-yl)-2-methylpropyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide

HRID 1397279Notes

Reaction equation

HRID 1397279 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]([CH3:17])([CH3:16])[CH2:14][NH2:15])[N:12]=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]=[C:27]([CH:31]=[CH:32][CH:33]=2)[C:28](O)=[O:29])[N:21]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]([CH3:17])([CH3:16])[CH2:14][NH:15][C:28](=[O:29])[C:27]3[CH:31]=[CH:32][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]=3)[N:12]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 673262552-(2-(4-Chlorophenyl)thiazol-4-yl)-2-methylpropan-1-amine

Product 1

HCID 67325170N-(2-(2-(4-chlorophenyl)thiazol-4-yl)-2-methylpropyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamideYield 25%

Procedure

This compound was synthesized from 2-(2-(4-chlorophenyl)thiazol-4-yl)-2-methylpropan-1-amine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (75 mg, yield 25%). 1H NMR (400 MHz, CDCl3) δ 8.53 (m, 1H), 8.27-8.25 (m, 1H), 8.10-8.05 (m, 2H), 7.86-7.84 (d, J=8.5 Hz, 2H), 7.62-7.59 (t, J=7.8 Hz, 1H), 7.33-7.31 (d, J=8.5 Hz, 2H), 7.08 (s, 1H), 3.71-3.69 (d, J=5.3 Hz, 2H), 1.49 (s, 6H). MS (ESI) m/z: Calculated for C23H18ClF3N4O2S: 506.08. found: 507.0 (M+H)+.

Sources & evidence

ORD record
ord-ceb9abd6c8274869824049ae662f0f8f
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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