p-Toluenesulfonic acid → 3-{2-[4-(4-Chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-[1,2,4]oxadiazol-3-yl-3H-benzooxazol-2-one

HRID 1710652Notes

Reaction equation

HRID 1710652 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:30])[CH2:15][N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25]([NH:27][OH:28])=[NH:26])=[CH:24][C:19]=4[O:18][C:17]3=[O:29])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:31][CH3:32].[CH:33](OC)(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14](=[O:30])[CH2:15][N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25]5[N:26]=[CH:33][O:28][N:27]=5)=[CH:24][C:19]=4[O:18][C:17]3=[O:29])[CH2:12][CH2:13]2)=[CH:4][C:3]=1[O:31][CH3:32]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 1784930233-[2-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]-2-oxoethyl]-N'-hydroxy-2-oxo-1,3-benzoxazole-6-carboximidamide

Product 1

HCID 160596303-{2-[4-(4-Chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-[1,2,4]oxadiazol-3-yl-3H-benzooxazol-2-one

Procedure

A mixture 3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-N-hydroxy-2-oxo-2,3-dihydro-benzooxazole-6-carboxamidine (65 mg), trimethyl orthoformate (3 ml) and p-toluenesulfonic acid (PTSA) (23 mg) was stirred at 103° C. overnight. The resultant solution was evaporated to dryness and then purified by flash chromatography to provide 3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-[1,2,4]oxadiazol-3-yl-3H-benzooxazol-2-one (51): LCMS observed for (M+H)+: 470.5.

Workup

  1. customThe resultant solution was evaporated to dryness
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-1ea2ececcf65455fa9727501b4b1f489
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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