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

HRID 1397309Notes

Reaction equation

HRID 1397309 reaction equation
[Cl: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>>[Cl: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 14977692-[4-(4-Chlorophenyl)-1,3-thiazol-2-yl]ethanamineHCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid

Product 1

HCID 67379497N-(2-(4-(4-Chlorophenyl)thiazol-2-yl)ethyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamideYield 16%

Procedure

This compound was synthesized from 2-(4-(4-chlorophenyl)thiazol-2-yl)ethanamine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (30 mg, yield 16%). 1H NMR (400 MHz, CDCl3) δ 8.53 (s, 1H), 8.26 (d, J=7.8 Hz, 1H), 8.06 (d, J=7.8 Hz, 1H), 7.81 (d, J=8.6 Hz, 2H), 7.64-7.60 (m, 2H), 7.39 (s, 1H), 7.34 (d, J=8.6 Hz, 2H), 4.02-3.97 (q, J=5.8 Hz, 2H), 3.39-3.36 (t, J=5.9 Hz, 2H). MS (ESI) m/z: Calculated for C21H14ClF3N4O2S: 478.05. found: 479.0 (M+H)+.

Sources & evidence

ORD record
ord-9dbc24d085f2476ca59a1e976bbe701d
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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