Dimethyl Sulfoxide → 4-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-3-ethyl-N,N-diisopropylpyridine-2-carboxamide

HRID 1645662Notes

Reaction equation

HRID 1645662 reaction equation
CS(C)=O.Cl[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]([N:14]([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])=[O:13])[C:7]=1[CH2:21][CH3:22].[H-].[Na+].[CH3:25][C:26]1([CH3:34])[O:31][CH2:30][CH:29]([CH2:32][OH:33])[CH2:28][O:27]1>C(OCC)(=O)C>[CH3:25][C:26]1([CH3:34])[O:31][CH2:30][CH:29]([CH2:32][O:33][C:6]2[CH:11]=[CH:10][N:9]=[C:8]([C:12]([N:14]([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])=[O:13])[C:7]=2[CH2:21][CH3:22])[CH2:28][O:27]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanolHCID 597924654-chloro-3-ethyl-N,N-diisopropylpyridine-2-carboxamide

Product 1

HCID 597925594-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-3-ethyl-N,N-diisopropylpyridine-2-carboxamideYield 36.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a dimethylsulfoxide (20 ml) solution of the 4-chloro-3-ethyl-N,N-diisopropylpyridine-2-carboxamide (1 g, 3.72 mmol) obtained in the step (92b) above, oily sodium hydride, in oil (195 mg, 4.46 mmol as the content was regarded as 55%) was added at room temperature. To the mixture, the (2,2-dimethyl-1,3-dioxan-5-yl)methanol (598 mg, 4.09 mmol) obtained in Example (11a) was added and the mixture was stirred at room temperature for 16.5 hours. Ethyl acetate was added to the reaction mixture. The mixture was washed twice with a saturate saline solution. The organic layer was dried over anhydrous magnesium sulfate, filtrated, and concentrated. The residue was washed with diethyl ether to obtain the title compound (520 mg, yield: 36.9%) as a light yellow solid.

Workup

  1. additionwas added at room temperature
  2. washThe mixture was washed twice with a saturate saline solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated
  6. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-14b96d5128c34a728dedda0f75466002
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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