Methanesulfonyl chloride → 2-[3-({[5-(5-Chloro-2-fluorophenyl)-1,2,4-oxadiazol-3-yl]methyl}thio)-5-(2-thienyl)-4H-1,2,4-triazol-4-yl]ethyl methanesulfonate

HRID 2102289Notes

Reaction equation

HRID 2102289 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6]([C:8]2[O:12][N:11]=[C:10]([CH2:13][S:14][C:15]3[N:19]([CH2:20][CH2:21][OH:22])[C:18]([C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)=[N:17][N:16]=3)[N:9]=2)[CH:7]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>CN(C=O)C.N1C=CC=CC=1>[CH3:29][S:30]([O:22][CH2:21][CH2:20][N:19]1[C:18]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[N:17][N:16]=[C:15]1[S:14][CH2:13][C:10]1[N:9]=[C:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[F:28])[O:12][N:11]=1)(=[O:32])=[O:31]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 670708392-{3-[5-(5-Chloro-2-fluoro-phenyl)-[1,2,4]oxadiazol-3-ylmethylsulfanyl]-5-thiophen-2-yl-[1,2,4]triazol-4-yl}-ethanol

Product 1

HCID 866025852-[3-({[5-(5-Chloro-2-fluorophenyl)-1,2,4-oxadiazol-3-yl]methyl}thio)-5-(2-thienyl)-4H-1,2,4-triazol-4-yl]ethyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[3-({[5-(5-chloro-2-fluorophenyl)-1,2,4-oxadiazol-3-yl]methyl}thio)-5-(2-thienyl)-4H-1,2,4-triazol-4-yl]ethanol in a mixture of DMF (1 ml) and pyridine (0.5 ml) was added methanesulfonyl chloride (20 uL). The mixture was stirred at r.t. for 24 h before poured onto water (10 ml). The crude product was filtered off and purified by chromatography on silica gel using 0-5% MeOH in DCM as eluent to give 43 mg of the title compound, which was used directly in the next step.

Workup

  1. additionbefore poured onto water (10 ml)
  2. filtrationThe crude product was filtered off
  3. custompurified by chromatography on silica gel using 0-5% MeOH in DCM as eluent

Sources & evidence

ORD record
ord-f9e3072143fa4ec48ea881121e9d2af8
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Reaction notes

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