3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 53327882, compound

HRID 874984Notes

Reaction equation

HRID 874984 reaction equation
OC(C(F)(F)F)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[C:17]([CH:20]3[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]3)[S:18][CH:19]=2)=[CH:11][CH:10]=1.[F:26][C:27]([F:43])([F:42])[C:28]1[O:32][N:31]=[C:30]([C:33]2[CH:34]=[C:35]([CH:39]=[CH:40][CH:41]=2)[C:36](O)=[O:37])[N:29]=1>>[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[C:17]([CH:20]3[CH2:25][CH2:24][CH2:23][N:22]([C:36]([C:35]4[CH:39]=[CH:40][CH:41]=[C:33]([C:30]5[N:29]=[C:28]([C:27]([F:42])([F:26])[F:43])[O:32][N:31]=5)[CH:34]=4)=[O:37])[CH2:21]3)[S:18][CH:19]=2)=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 86673535HCID 86673535, compound

Product 1

HCID 53327882HCID 53327882, compoundYield 28%

Procedure

This compound was synthesized from 4-(4-fluorophenyl)-2-(piperidin-3-yl)thiazole TFA salt and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (41 mg, yield 28%). 1H NMR (400 MHz, MeOD) δ 8.20-8.18 (m, 1H), 8.09 (m, 1H), 7.85 (m, 2H), 7.66-7.65 (d, J=4.3 Hz, 2H), 7.59 (m, 1H), 7.10-7.05 (t, J=8.4 Hz, 2H), 3.91 (m, 1H), 3.65 (m, 1H), 3.49-3.39 (m, 2H), 2.36-2.31 (m, 1H), 2.12-2.03 (m, 3H), 1.77-1.74 (m, 1H). MS (ESI) m/z: Calculated for C24H18F4N4O2S: 502.11. found: 503.1 (M+H)+

Sources & evidence

ORD record
ord-af63bf3e75fc420084bc14f7be8bcf30
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

Loading…