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

HRID 875033Notes

Reaction equation

HRID 875033 reaction equation
OC(C(F)(F)F)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][CH:17]=[C:18]([CH2:20][N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:19]=2)=[CH:11][CH:10]=1.[F:27][C:28]([F:44])([F:43])[C:29]1[O:33][N:32]=[C:31]([C:34]2[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=2)[C:37](O)=[O:38])[N:30]=1>>[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][CH:17]=[C:18]([CH2:20][N:21]3[CH2:22][CH2:23][N:24]([C:37]([C:36]4[CH:40]=[CH:41][CH:42]=[C:34]([C:31]5[N:30]=[C:29]([C:28]([F:43])([F:27])[F:44])[O:33][N:32]=5)[CH:35]=4)=[O:38])[CH2:25][CH2:26]3)[N:19]=2)=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 866735412-(4-Fluorophenyl)-4-(piperazin-1-ylmethyl)oxazole TFA Salt

Product 1

HCID 53327949(4-((2-(4-Fluorophenyl)oxazol-4-yl)methyl)piperazin-1-yl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)methanoneYield 14%

Procedure

This compound was synthesized from 2-(4-fluorophenyl)-4-(piperazin-1-ylmethyl)oxazole TFA salt and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (34 mg, yield 14%). 1H NMR (400 MHz, CDCl3) δ 8.19-8.17 (m, 2H), 8.06-8.03 (dd, J=8.7 Hz, 5.1 Hz, 2H), 7.63-7.57 (m, 3H), 7.17-7.12 (t, J=8.7 Hz, 2H), 3.87 (m, 2H), 3.59 (s, 2H), 3.50 (m, 2H), 2.68 (m, 2H), 2.54 (m, 2H). MS (ESI) m/z: Calculated for C24H19F4N6O3: 501.14. found: 502.1 (M+H)+

Sources & evidence

ORD record
ord-dc14591d37f84194936a67545761294f
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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