2-(2-(4-Chlorophenyl)thiazol-4-yl)ethanamine → N-(2-(2-(4-Chlorophenyl)thiazol-4-yl)ethyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide

HRID 1397304Notes

Reaction equation

HRID 1397304 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][CH2:14][NH2:15])[N:12]=2)=[CH:4][CH:3]=1.[F:16][C:17]([F:33])([F:32])[C:18]1[O:22][N:21]=[C:20]([C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=2)[C:26](O)=[O:27])[N:19]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][CH2:14][NH:15][C:26](=[O:27])[C:25]3[CH:29]=[CH:30][CH:31]=[C:23]([C:20]4[N:19]=[C:18]([C:17]([F:33])([F:32])[F:16])[O:22][N:21]=4)[CH:24]=3)[N:12]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 226902632-(2-(4-Chlorophenyl)thiazol-4-yl)ethanamineHCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid

Product 1

HCID 67379024N-(2-(2-(4-Chlorophenyl)thiazol-4-yl)ethyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamideYield 22%

Procedure

This compound was synthesized from 2-(2-(4-chlorophenyl)thiazol-4-yl)ethanamine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (40 mg, yield 22%). 1H NMR (400 MHz, CDCl3) δ 8.53 (t, J=1.5 Hz, 1H), 8.27-8.25 (dt, J=7.8 Hz, 1.3 Hz, 1H), 8.09-8.07 (dt, J=7.8 Hz, 1.4 Hz, 1H), 7.89-7.87 (m, 2H), 7.68 (m, 1H), 7.62 (t, J=7.8 Hz, 1H), 7.36-7.34 (m, 2H), 7.09 (s, 1H), 3.92-3.87 (m, 2H), 3.16 (t, J=6.0 Hz, 2H). MS (ESI) m/z: Calculated for C21H14ClF3N4O2S: 478.05. found: 479.0 (M+H)+.

Sources & evidence

ORD record
ord-6d9e4c7974914f6287d37656134235e9
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

Loading…