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]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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
- additionwas added at room temperature
- washThe mixture was washed twice with a saturate saline solution
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltrated
- concentrationconcentrated
- washThe residue was washed with diethyl ether
Sources & evidence
- ORD record
- ord-faf7a348652c48d4ac613a0eb85291d2
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07425634B2
Linked notes
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