Potassium Carbonate → 2-{3-[5-(5-Chloro-2-fluoro-phenyl)-[1,2,4]oxadiazol-3-ylmethylsulfanyl]-5-thiophen-2-yl-[1,2,4]triazol-4-yl}-ethanol

HRID 2102288Notes

Reaction equation

HRID 2102288 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[N:7][NH:6][C:5]1=[S:14].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([F:29])=[C:20]([C:22]2[O:26][N:25]=[C:24]([CH2:27]Cl)[N:23]=2)[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CC#N>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([F:29])=[C:20]([C:22]2[O:26][N:25]=[C:24]([CH2:27][S:14][C:5]3[N:4]([CH2:3][CH2:2][OH:1])[C:8]([C:9]4[S:10][CH:11]=[CH:12][CH:13]=4)=[N:7][N:6]=3)[N:23]=2)[CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 431202105-(5-Chloro-2-fluoro-phenyl)-3-chloromethyl-[1,2,4]oxadiazoleHCID 859371364-(2-Hydroxy-ethyl)-5-thiophen-2-yl-2,4-dihydro-[1,2,4]triazole-3-thione

Product 1

HCID 670708392-{3-[5-(5-Chloro-2-fluoro-phenyl)-[1,2,4]oxadiazol-3-ylmethylsulfanyl]-5-thiophen-2-yl-[1,2,4]triazol-4-yl}-ethanolYield 62.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

4-(2-Hydroxyethyl)-5-(2-thienyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (101 mg), 5-(5-chloro-2-fluorophenyl)-3-(chloromethyl)-1,2,4-oxadiazole (116 mg), and potassium carbonate (86 mg) was stirred in a mixture of DMF (2 ml) and MeCN (15 ml) at r.t. for 3 h before concentration to dryness and washing of the residue with water, and then with EtOAc, to provide 122 mg of the title compound as a white solid.

Workup

  1. washwashing of the residue with water

Sources & evidence

ORD record
ord-df3c4fe9e7984acf97574141a8fa93b0
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Reaction notes

Loading…