3-(4-Phenylthiazol-2-yl)propan-1-amine → N-(3-(4-Phenylthiazol-2-yl)propyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide

HRID 1397337Notes

Reaction equation

HRID 1397337 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][CH2:13][CH2:14][NH2:15])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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>>[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][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:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 242618563-(4-Phenylthiazol-2-yl)propan-1-amineHCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid

Product 1

HCID 67379223N-(3-(4-Phenylthiazol-2-yl)propyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamideYield 70%

Procedure

This compound was synthesized from 3-(4-phenylthiazol-2-yl)propan-1-amine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (100 mg, yield 70%). 1H NMR (400 MHz, CDCl3) δ 8.40 (m, 1H), 8.17-8.14 (m, 1H), 7.96-7.94 (m, 1H), 7.80-7.78 (m, 2H), 7.45-7.41 (m, 1H), 7.34-7.29 (m, 4H), 3.70-3.66 (q, J=6.3 Hz, 2H), 3.27-3.23 (t, J=6.7 Hz, 2H), 2.29-2.23 (m, 2H). MS (ESI) m/z: Calculated for C22H17F3N4O2S: 458.10. found: 459.2 (M+H)+.

Sources & evidence

ORD record
ord-3b6c84c86ba14c6f9240aab77b3d4ca6
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

Loading…