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

HRID 1397250Notes

Reaction equation

HRID 1397250 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][NH2:15])[S:11][CH: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>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([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)[S:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 46549852-(4-(4-Fluorophenyl)thiazol-2-yl)ethanamineHCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid

Product 1

HCID 67343946N-(2-(4-(4-Fluorophenyl)thiazol-2-yl)ethyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamideYield 86%

Procedure

This compound was synthesized from 2-(4-(4-fluorophenyl)thiazol-2-yl)ethanamine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 26 step 6 (180 mg, 86% yield). 1H NMR (CDCl3) δ 8.51 (1H, t), 8.22 (1H, dt), 8.04 (1H, dt), 7.85-7.81 (2H, m), 7.64 (1H, m), 7.59 (1H, t), 7.31 (1H, s), 7.06-7.02 (2H, m), 3.97 (2H, q), 3.35 (2H, t); MS (ESI) m/z: Calculated for C21H14F4N4O2S: 462.08. found: 463.1 (M+H)+.

Sources & evidence

ORD record
ord-05c8a8d120b242e194708ce062decdfa
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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