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

HRID 1397396Notes

Reaction equation

HRID 1397396 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[N:6]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[O:8][CH:9]=1)[OH:4].[F:17][C:18]([F:34])([F:33])[C:19]1[O:23][N:22]=[C:21]([C:24]2[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=2)[C:27](O)=[O:28])[N:20]=1>>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2[O:8][CH:9]=[C:5]([CH:3]([OH:4])[CH2:2][NH:1][C:27](=[O:28])[C:26]3[CH:30]=[CH:31][CH:32]=[C:24]([C:21]4[N:20]=[C:19]([C:18]([F:34])([F:33])[F:17])[O:23][N:22]=4)[CH:25]=3)[N:6]=2)=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 673224952-Amino-1-(2-(4-fluorophenyl)oxazol-4-yl)ethanol

Product 1

HCID 67326379N-(2-(2-(4-Fluorophenyl)oxazol-4-yl)-2-hydroxyethyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamideYield 39%

Procedure

This compound was synthesized from 2-amino-1-(2-(4-fluorophenyl)oxazol-4-yl)ethanol and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (70 mg, yield 39%). 1H NMR (400 MHz, CDCl3) δ 8.51 (m, 1H), 8.28-8.26 (m, 1H), 8.08-8.01 (m, 3H), 7.73 (s, 1H), 7.66-7.62 (m, 1H), 7.17-7.08 (m, 3H), 5.05-5.03 (m, 1H), 4.12-4.06 (ddd, J=14.1 Hz, 6.3 Hz, 3.8 Hz, 1H), 3.91-3.85 (m, 1H), 3.77 (br s, 1H). MS (ESI) m/z: Calculated for C21H14F4N4O4: 462.10. found: 463.1 (M+H)+.

Sources & evidence

ORD record
ord-35abc06b393f4d2abe82c05cc16f2904
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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