3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)aniline → 3-(4-(4-Fluorophenyl)thiazol-2-yl)-N-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)propanamide

HRID 1397303Notes

Reaction equation

HRID 1397303 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=2)[NH2:11])[N:4]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:25]=[C:26]([CH2:29][CH2:30][C:31](O)=[O:32])[S:27][CH:28]=2)=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[N:25]=[C:26]([CH2:29][CH2:30][C:31]([NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[C:8]([C:5]4[N:4]=[C:3]([C:2]([F:15])([F:1])[F:16])[O:7][N:6]=4)[CH:9]=3)=[O:32])[S:27][CH:28]=2)=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 202975493-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)anilineHCID 393539643-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]propanoic acid

Product 1

HCID 673249353-(4-(4-Fluorophenyl)thiazol-2-yl)-N-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)propanamideYield 43%

Procedure

This compound was synthesized from 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)aniline and 3-(4-(4-fluorophenyl)thiazol-2-yl)propanoic acid as described in example 8 step 6 (80 mg, yield 43%). 1H NMR (400 MHz, CDCl3) δ 8.80 (br s, 1H), 8.11 (s, 1H), 7.88-7.83 (m, 4H), 7.48-7.44 (t, J=7.9 Hz, 1H), 7.33 (s, 1H), 7.14-7.10 (t, J=8.7 Hz, 2H), 3.52-3.48 (m, 2H), 3.04-3.01 (m, 2H). MS (ESI) m/z: Calculated for C21H14F4N4O2S: 462.08. found: 463.0 (M+H)+.

Sources & evidence

ORD record
ord-1f44fe70e1674ddf8ccfe46a4f782336
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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