Trifluoroacetic acid → 3-{2-[4-(4-Chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-(2-hydroxy-ethoxy)-3H-benzooxazol-2-one

HRID 1710656Notes

Reaction equation

HRID 1710656 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:36])[CH2:15][N:16]3[C:20]4[CH:21]=[CH:22][C:23]([O:25][CH2:26][CH2:27][O:28]C5CCCCO5)=[CH:24][C:19]=4[O:18][C:17]3=[O:35])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:37][CH3:38].C(O)(C(F)(F)F)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14](=[O:36])[CH2:15][N:16]3[C:20]4[CH:21]=[CH:22][C:23]([O:25][CH2:26][CH2:27][OH:28])=[CH:24][C:19]=4[O:18][C:17]3=[O:35])[CH2:12][CH2:13]2)=[CH:4][C:3]=1[O:37][CH3:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 588343673-{2-[4-(4-Chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-3H-benzooxazol-2-one

Product 1

HCID 160596313-{2-[4-(4-Chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-(2-hydroxy-ethoxy)-3H-benzooxazol-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-3H-benzooxazol-2-one (55) (50 mg) in THF was added 1 mL of TFA and the resultant solution was stirred for 1 hour. The reaction mixture was purified by HPLC to provide 3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-(2-hydroxy-ethoxy)-3H-benzooxazol-2-one (56): LCMS observed for (M+H)+: 462.5.

Workup

  1. customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record
ord-4232207898834dd896d91245483f3bb9
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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