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

HRID 1397358Notes

Reaction equation

HRID 1397358 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][NH2:14])[N:12]=2)=[CH:4][CH:3]=1.[F:15][C:16]([F:32])([F:31])[C:17]1[O:21][N:20]=[C:19]([C:22]2[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=2)[C:25](O)=[O:26])[N:18]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][NH:14][C:25](=[O:26])[C:24]3[CH:28]=[CH:29][CH:30]=[C:22]([C:19]4[N:18]=[C:17]([C:16]([F:32])([F:31])[F:15])[O:21][N:20]=4)[CH:23]=3)[N:12]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 28287570(2-(4-Fluorophenyl)oxazol-4-YL)methanamine

Product 1

HCID 67347884N-((2-(4-Fluorophenyl)oxazol-4-yl)methyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamideYield 26%

Procedure

This compound was synthesized from (2-(4-fluorophenyl)oxazol-4-yl)methanamine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (65 mg, yield 26%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.35-9.32 (m, 1H), 8.60 (t, J=1.5 Hz, 1H), 8.25-8.19 (m, 2H), 8.12 (m, 1H), 8.04-8.00 (m, 2H), 7.77-7.73 (t, J=7.8 Hz, 1H), 7.41-7.36 (m, 2H), 4.48-4.47 (d, J=5.2 Hz, 2H). MS (ESI) m/z: Calculated for C20H12F4N4O3: 432.08. found: 433.2 (M+H)+.

Sources & evidence

ORD record
ord-fba3b87f476b4f29a4778e06cd98ea15
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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