Water → (2-Fluoro-6-isopropoxy-3-methanesulfonyl-phenyl)-[4-(2-fluoro-4-methanesulfonyl-phenyl)-piperazin-1-yl]-methanone

HRID 1820773Notes

Reaction equation

HRID 1820773 reaction equation
[F:1][C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=O)=[CH:6][CH:5]=[C:4](F)[C:3]=1[C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][C:22]=2[F:31])[CH2:17][CH2:16]1)=[O:14].[CH:32]([O-:35])([CH3:34])[CH3:33].[Na+].[OH2:37]>>[F:1][C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:37])=[CH:6][CH:5]=[C:4]([O:35][CH:32]([CH3:34])[CH3:33])[C:3]=1[C:13]([N:15]1[CH2:16][CH2:17][N:18]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][C:22]=2[F:31])[CH2:19][CH2:20]1)=[O:14]

Participants

4

Reactant 3

HCID 962WaterHCID 109204432-Propanol, sodium salt (1:1)HCID 69037451(2,6-Difluoro-3-methanesulfonyl-phenyl)-[4-(2-fluoro-4-methanesulfonyl-phenyl)-piperazin-1-yl]-methanone

Product 1

HCID 69036831(2-Fluoro-6-isopropoxy-3-methanesulfonyl-phenyl)-[4-(2-fluoro-4-methanesulfonyl-phenyl)-piperazin-1-yl]-methanone

Conditions

Temperature
50 °C

Procedure

0.2 mmol of (2,6-difluoro-3-methanesulfonyl-phenyl)-[4-(2-fluoro-4-methanesulfonyl-phenyl)-piperazin-1-yl]-methanone were dissolved in a solution of sodium isopropanolate (prepared by dissolving 0.2 mmol of sodium in 1 ml of isopropanol). The reaction mixture was heated to 50° C. for 2 hours, then stirred at room temperature for 48 hours. The solution was diluted with water and extracted with ethyl acetate. The product was purified by chromatography (SiO2, ethyl acetate/cyclohexane 9:1) to yield the title compound as a colorless solid. MS (m/e): 517.1 (MH+, 100%)

Workup

  1. extractionextracted with ethyl acetate
  2. customThe product was purified by chromatography (SiO2, ethyl acetate/cyclohexane 9:1)

Sources & evidence

ORD record
ord-498a7b7c2d374a14ada727eaa6eade81
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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