Sodium Hydroxide → HCID 57753038, compound

HRID 225449Notes

Reaction equation

HRID 225449 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([C:10]2[C:14]3[N:15]=[C:16]([CH3:28])[N:17]=[C:18]([N:19]4[CH2:24][CH2:23][CH:22]([CH2:25][C:26]#[N:27])[CH2:21][CH2:20]4)[C:13]=3[S:12][C:11]=2[CH3:29])=[C:5]([CH3:30])[CH:4]=1.[OH-].[Na+].C([O-])(O)=[O:34].[Na+]>OS(O)(=O)=O>[Br:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([C:10]2[C:14]3[N:15]=[C:16]([CH3:28])[N:17]=[C:18]([N:19]4[CH2:20][CH2:21][CH:22]([CH2:25][C:26]([NH2:27])=[O:34])[CH2:23][CH2:24]4)[C:13]=3[S:12][C:11]=2[CH3:29])=[C:5]([CH3:30])[CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 68828329HCID 68828329, compound

Product 1

HCID 57753038HCID 57753038, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

{1-[7-(4-Bromo-2,6-dimethyl-phenyl)-2,6-dimethyl-thieno[3,2-d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile hydrochloride (30 mg) was dissolved in c H2SO4 (0.5 mL) and the solution was stirred at room temperature for 20 hours. After addition of ice, the reaction mixture was made to alkaline (pH 7) with an aqueous NaOH solution and an aqueous NaHCO3 solution. The mixture was extracted with EtOAc and the organic layer washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: EtOAc) to obtain the title compound (20 mg) as a white crystal.

Workup

  1. additionAfter addition of ice
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic layer washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: EtOAc)

Sources & evidence

ORD record
ord-6f24bf08b5414949b0f9f0ceb22bb47f
Source dataset
uspto-grants-2009_07
Patent number
US07557111B2

Reaction notes

Loading…