Water → HCID 66750858, compound

HRID 535002Notes

Reaction equation

HRID 535002 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[N:12]1[CH2:17][CH2:16][N:15]([C:18]([C:20]2[N:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[O:19])[CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[N:12]1[CH2:13][CH2:14][N:15]([C:18]([C:20]2[N:25]=[CH:24][C:23]([O:26][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:22][CH:21]=2)=[O:19])[CH2:16][CH2:17]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 66792790HCID 66792790, compound

Product 1

HCID 66750858HCID 66750858, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-{[4-(2-tert-butyl-4-chlorophenyl)piperazin-1-yl]carbonyl}pyridin-3-ol (Example 208, 0.26 g, 0.69 mmol), methyl bromoacetate (0.13 g, 0.82 mmol) and potassium carbonate (0.19 g, 1.38 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 2 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was filtered through NH-silica gel pad to give the title compound (0.27 g, 89%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe residue was filtered through NH-silica gel pad

Sources & evidence

ORD record
ord-1b5a008ea38145db91401f339d387e00
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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