Ethyl bromoacetate → {4-[2-(2,3-Difluoro-benzylsulfanyl)-6-methoxy-pyrimidin-4-ylsulfamoyl]-piperazin-1-yl}-acetic acid ethyl ester

HRID 2388855Notes

Reaction equation

HRID 2388855 reaction equation
[H-].[Na+].FC(F)(F)C(O)=O.[F:10][C:11]1[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:18][S:19][C:20]1[N:25]=[C:24]([NH:26][S:27]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)(=[O:29])=[O:28])[CH:23]=[C:22]([O:36][CH3:37])[N:21]=1.Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>C1COCC1.O>[CH2:43]([O:42][C:40](=[O:41])[CH2:39][N:33]1[CH2:32][CH2:31][N:30]([S:27](=[O:29])(=[O:28])[NH:26][C:24]2[CH:23]=[C:22]([O:36][CH3:37])[N:21]=[C:20]([S:19][CH2:18][C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([F:17])[C:11]=3[F:10])[N:25]=2)[CH2:35][CH2:34]1)[CH3:44]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 67051309N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-methoxypyrimidin-4-yl]piperazine-1-sulfonamide, trifluoroacetate salt2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The subtitle compound was prepared by adding 60% sodium hydride (0.18 g) portionwise to a solution of N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-methoxypyrimidin-4-yl]piperazine-1-sulfonamide, trifluoroacetate salt (the product from example 36) (0.53 g) and ethyl 2-bromoacetate (0.36 mL) in THF (10 mL). The reaction mixture was diluted with H2O and extracted with EtOAc. The organic layer was washed with brine and evaporated to give the subtitle compound as an oil.

Workup

  1. customThe subtitle compound was prepared
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. customevaporated

Sources & evidence

ORD record
ord-cab974ba92634ee8b33580d2039acf37
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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