3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → (4-Methyl-3-(4-phenylthiazol-2-yl)piperazin-1-yl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)methanone

HRID 874971Notes

Reaction equation

HRID 874971 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH:3]1[C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:12]=1.[F:19][C:20]([F:36])([F:35])[C:21]1[O:25][N:24]=[C:23]([C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=2)[C:29](O)=[O:30])[N:22]=1>>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:29]([C:28]2[CH:32]=[CH:33][CH:34]=[C:26]([C:23]3[N:22]=[C:21]([C:20]([F:35])([F:19])[F:36])[O:25][N:24]=3)[CH:27]=2)=[O:30])[CH2:4][CH:3]1[C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:12]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 673249512-(1-Methylpiperazin-2-yl)-4-phenylthiazole

Product 1

HCID 53327857(4-Methyl-3-(4-phenylthiazol-2-yl)piperazin-1-yl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)methanoneYield 32%

Procedure

This compound was synthesized from 2-(1-methylpiperazin-2-yl)-4-phenylthiazole and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (30 mg, yield 32%) as colorless viscous liquid. 1H NMR (400 MHz, CDCl3) δ 8.17-8.16 (m, 2H), 7.93-7.79 (m, 2H), 7.64-7.62 (m, 2H), 7.48-7.32 (m, 4H), 4.78-4.53 (m, 1H), 3.85-3.69 (m, 2H), 3.49-3.30 (m, 2H), 3.17-2.98 (m, 1H), 2.53-2.40 (m, 1H), 2.32 (s, 3H). MS (ESI) m/z: Calculated for C24H20F3N5O2S: 499.12. found: 500.2 (M+H)+

Sources & evidence

ORD record
ord-987c468b229d468bbd8a052a87f07862
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

Loading…