3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → N-((4-(4-(4-Fluorophenyl)thiazol-2-yl)-2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide

HRID 1397255Notes

Reaction equation

HRID 1397255 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]3([CH2:21][NH2:22])[CH2:18][CH2:17][O:16][C:15]([CH3:20])([CH3:19])[CH2:14]3)[S:11][CH:12]=2)=[CH:4][CH:3]=1.[F:23][C:24]([F:40])([F:39])[C:25]1[O:29][N:28]=[C:27]([C:30]2[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=2)[C:33](O)=[O:34])[N:26]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]3([CH2:21][NH:22][C:33](=[O:34])[C:32]4[CH:36]=[CH:37][CH:38]=[C:30]([C:27]5[N:26]=[C:25]([C:24]([F:40])([F:39])[F:23])[O:29][N:28]=5)[CH:31]=4)[CH2:18][CH2:17][O:16][C:15]([CH3:19])([CH3:20])[CH2:14]3)[S:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67325652HCID 67325652, compound

Product 1

HCID 69950049N-((4-(4-(4-Fluorophenyl)thiazol-2-yl)-2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamideYield 17%

Procedure

This compound was synthesized from (4-(4-(4-fluorophenyl)thiazol-2-yl)-2,2-dimethyltetrahydro-2H-pyran-4-yl)methanamine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (7 mg, yield 17%): 1H NMR (500 MHz, CD3OD) δ 8.41 (t, J=1 Hz, 1H), 8.23 (d, J=4 Hz, 1H), 7.96-7.90 (m, 3H), 7.76 (s, 1H), 7.61 (t, J=7.7 Hz, 1H), 7.69-7.04 (t, J=8.8 Hz, 2H), 3.88 (m, 2H), 3.60 (s, 2H), 2.52 (m, 2H), 1.95 (m, 2H), 1.29 (s, 3H), 0.81 (s, 3H). MS (ESI) m/z: Calculated for C27H24F4N4O3S: 560.15. found: 561.1 (M+H)+.

Sources & evidence

ORD record
ord-436cd8e804d746deaaba4803570dc388
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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