Dimethylamine, hydrochloride → HCID 67012493, compound

HRID 1966939Notes

Reaction equation

HRID 1966939 reaction equation
[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:23][C@H:22]([CH2:24]OS(C)(=O)=O)[O:21][C:20]4=[O:30])=[CH:15][C:14]=3[F:31])=[CH:9][N:8]=2)=[N:3]1.Cl.[CH3:33][NH:34][CH3:35]>CN(C)C=O>[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:23][C@@H:22]([CH2:24][N:34]([CH3:35])[CH3:33])[O:21][C:20]4=[O:30])=[CH:15][C:14]=3[F:31])=[CH:9][N:8]=2)=[N:3]1

Participants

4

Reactant 2

HCID 10473Dimethylamine, hydrochlorideHCID 52916241HCID 52916241, compound

Product 1

HCID 67012493HCID 67012493, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

In 5 ml of dimethylformamide was dissolved 100 mg of (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-methanesulfonyloxymethyl oxazolidin-2-one prepared in the secondary step of the Example 24. The solution was added with 30 mg of dimethylamine hydrochloride at room temperature. The solution was stirred for 30 hours at the temperature of 60° C. And then the solution was extracted with ethyl acetate and the organic layer, thus separated, was washed with water and brine. The residue, prepared by dehydrating, filtering and concentrating the organic layer, was purified by column chromatography to provide the title compound 70 mg. Yield 76%.

Workup

  1. customprepared in the secondary step of the Example 24
  2. extractionAnd then the solution was extracted with ethyl acetate
  3. customthe organic layer, thus separated
  4. washwas washed with water and brine
  5. customThe residue, prepared
  6. filtrationfiltering
  7. concentrationconcentrating the organic layer
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-1e4572bb33e94c77b903d71e974288d9
Source dataset
uspto-grants-2013_04
Patent number
US08420676B2

Reaction notes

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