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

HRID 874998Notes

Reaction equation

HRID 874998 reaction equation
OC(C(F)(F)F)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][C:18]([CH:20]3[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]3)=[N:17][CH:16]=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[O:19][C:18]([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)=[N:17][CH:16]=2)=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 866735365-(4-Fluorophenyl)-2-(piperidin-3-yl)oxazole TFA Salt

Product 1

HCID 53327886(3-(5-(4-Fluorophenyl)oxazol-2-yl)piperidin-1-yl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)methanoneYield 9%

Procedure

This compound was synthesized from 5-(4-fluorophenyl)-2-(piperidin-3-yl)oxazole TFA salt and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (25 mg, yield 9%). 1H NMR (400 MHz, DMSO-d6, 80° C.) δ 8.11-8.09 (m, 1H), 7.97 (s, 1H), 7.69-7.61 (m, 4H), 7.45 (s, 1H), 7.24-7.20 (t, J=8.8 Hz, 2H), 4.16 (m, 1H), 3.71-3.67 (m, 1H), 3.62-3.56 (dd, J=12.9 Hz, 8.4 Hz, 1H), 3.47-3.41 (m, 1H), 3.24-3.18 (m, 1H), 2.22-2.17 (m, 1H), 2.03-1.94 (m, 1H), 1.89-1.84 (m, 1H), 1.69-1.59 (m, 1H). MS (ESI) m/z: Calculated for C24H18F4N4O3: 486.13. found: 487.3 (M+H)+

Sources & evidence

ORD record
ord-0a6b8e10e9314a6fba92e2cd97e1c617
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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