2-Amino-1-(2-(4-fluorophenyl)oxazol-4-yl)ethanol → N-(2-(2-(4-Fluorophenyl)oxazol-4-yl)-2-hydroxyethyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide

HRID 1397409Notes

Reaction equation

HRID 1397409 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]=[N:26][CH:27]=[C:28]([CH:32]=2)[C:29](O)=[O:30])[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:29](=[O:30])[C:28]3[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]=[N:26][CH:27]=3)[N:6]=2)=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 673224952-Amino-1-(2-(4-fluorophenyl)oxazol-4-yl)ethanolHCID 673242165-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid

Product 1

HCID 53345246N-(2-(2-(4-Fluorophenyl)oxazol-4-yl)-2-hydroxyethyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamideYield 45%

Procedure

This compound was synthesized from 2-amino-1-(2-(4-fluorophenyl)oxazol-4-yl)ethanol and 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid as described in example 8 step 6 (120 mg, yield 45%). 1H NMR (400 MHz, DMSO-d6) δ 9.35 (d, J=1.8 Hz, 1H), 9.27 (d, J=1.8 Hz, 1H), 9.13-9.10 (t, J=5.6 Hz, 1H), 8.84-8.83 (t, J=1.8 Hz, 1H), 8.11 (s, 1H), 8.03-8.00 (dd, J=8.5 Hz, 5.5 Hz, 2H), 7.39-7.35 (t, J=8.9 Hz, 2H), 5.74-5.73 (d, J=5.2 Hz, 1H), 4.85-4.81 (m, 1H), 3.77-3.71 (m, 1H), 3.56-3.49 (m, 1H). MS (ESI) m/z: Calculated for C20H13F4N5O4: 463.09. found: 464.0 (M+H)+.

Sources & evidence

ORD record
ord-eae05e78e623416788f82c46f06194e4
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

Loading…