N,N-Dimethylaniline → HCID 22272855, compound

HRID 1064857Notes

Reaction equation

HRID 1064857 reaction equation
[NH2:1][C:2]1[C:3]([S:11][CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[N:4][C:5]([CH3:10])=[CH:6][C:7]=1[S:8][CH3:9].CN(C)C1C=CC=CC=1.[Br:31][CH2:32][C:33](Br)=[O:34].[Cl-].[NH4+]>ClCCl>[Br:31][CH2:32][C:33]([NH:1][C:2]1[C:3]([S:11][CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17])=[N:4][C:5]([CH3:10])=[CH:6][C:7]=1[S:8][CH3:9])=[O:34]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 25517Ammonium ChlorideHCID 61147Bromoacetyl bromideHCID 22272807HCID 22272807, compound

Product 1

HCID 22272855HCID 22272855, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-2-(2-tert-butyldimethylsilyloxyethylthio)-6-methyl-4-methylthiopyridine (synthesized by the method disclosed in Example 30 in WO96/26925) (1.50 g, 4.35 mmol) in dichloromethane (30 ml) were added N,N-dimethylaniline (0.63 g, 5.22 mmol) and bromoacetyl bromide (1.05 g, 5.22 mmol) with ice-cooling and stirring, and the mixture was stirred at room temperature for 1 hour. The reaction solution was mixed with a saturated ammonium chloride solution and extracted with chloroform. The organic layer was washed with water and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (silica gel 100 g, developing solvent; hexane:ethyl acetate=3:1) to provide 1.57 g (yield 78%) of 2-bromo-N-[2-(2-tert-butyldimethylsilyloxyethylthio)-6-methyl-4-methylthio-3-pyridyl]acetamide as colorless powdery crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water
  5. dry with materiala saturated sodium chloride solution successively, dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by a silica gel column chromatography (silica gel 100 g, developing solvent; hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-17edd6ee72f24f40b5d1e11d7086e636
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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