3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → (4-(4-Phenylpyrimidin-2-yl)piperazin-1-yl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)methanone

HRID 875007Notes

Reaction equation

HRID 875007 reaction equation
OC(C(F)(F)F)=O.[C:8]1([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[N:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=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>>[C:8]1([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([N:20]3[CH2:25][CH2:24][N:23]([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])[CH2:22][CH2:21]3)[N:15]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 866735384-Phenyl-2-(piperazin-1-yl)pyrimidine TFA Salt

Product 1

HCID 53327904(4-(4-Phenylpyrimidin-2-yl)piperazin-1-yl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)methanoneYield 53%

Procedure

This compound was synthesized from 4-phenyl-2-(piperazin-1-yl)pyrimidine TFA salt and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (100 mg, yield 53%). 1H NMR (400 MHz, MeOD) δ 8.31-8.25 (m, 5H), 7.78-7.72 (m, 2H), 7.47-7.45 (m, 3H), 6.77-6.75 (d, J=6.3 Hz, 1H), 3.99-3.87 (m, 6H), 3.66 (s, 2H). MS (ESI) m/z: Calculated for C24H19F3N6O2: 480.15. found: 481.2 (M+H)+

Sources & evidence

ORD record
ord-c77b0d97b98a4fedbbb868290fd6113d
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

Loading…