Sodium Hydroxide → {4-[2-(2,3-Difluoro-benzylsulfanyl)-6-methoxy-pyrimidin-4-ylsulfamoyl]-piperazin-1-yl}-acetic acid

HRID 1175486Notes

Reaction equation

HRID 1175486 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:36])[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([S:14](=[O:35])(=[O:34])[NH:15][C:16]2[CH:21]=[C:20]([O:22][CH3:23])[N:19]=[C:18]([S:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=3[F:33])[N:17]=2)[CH2:10][CH2:9]1)C>CO>[F:33][C:27]1[C:28]([F:32])=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][S:24][C:18]1[N:17]=[C:16]([NH:15][S:14]([N:11]2[CH2:10][CH2:9][N:8]([CH2:7][C:6]([OH:36])=[O:5])[CH2:13][CH2:12]2)(=[O:34])=[O:35])[CH:21]=[C:20]([O:22][CH3:23])[N:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53628396{4-[2-(2,3-Difluoro-benzylsulfanyl)-6-methoxy-pyrimidin-4-ylsulfamoyl]-piperazin-1-yl}-acetic acid ethyl ester

Product 1

HCID 59558754{4-[2-(2,3-Difluoro-benzylsulfanyl)-6-methoxy-pyrimidin-4-ylsulfamoyl]-piperazin-1-yl}-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared by adding 1M NaOH (1 mL) to a solution of {4-[2-(2,3-Difluoro-benzylsulfanyl)-6-methoxy-pyrimidin-4-ylsulfamoyl]-piperazin-1-yl}-acetic acid ethyl ester (the product from step i) (0.31 g) in MeOH (1 mL). Purification was by reverse phase HPLC (symmetry as the stationary phase and TFA/acetonitrile as the mobile phase) then titurated with Toluene, DCM followed by Et2O to give the title compound as a white solid. Yield: 85 mg

Workup

  1. customThe title compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-1253e4974214478e8e8c6cdee7aa8b21
Source dataset
uspto-grants-2010_11
Patent number
US07838675B2

Reaction notes

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