Dimethylformamide → HCID 67973424, compound

HRID 623904Notes

Reaction equation

HRID 623904 reaction equation
[H-].[Na+].CN(C)C=O.[CH3:8][C:9]([CH3:38])([CH2:14][O:15][C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([C:23]2[CH:28]=[N:27][C:26]([C:29]3[NH:30][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:32][N:33]=3)=[CH:25][N:24]=2)=[CH:18][N:17]=1)[C:10]([O:12][CH3:13])=[O:11].[CH3:39][Si:40]([CH3:47])([CH3:46])[CH2:41][CH2:42][O:43][CH2:44]Cl>O>[CH3:8][C:9]([CH3:38])([CH2:14][O:15][C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([C:23]2[CH:28]=[N:27][C:26]([C:29]3[N:33]([CH2:44][O:43][CH2:42][CH2:41][Si:40]([CH3:47])([CH3:46])[CH3:39])[CH:32]=[C:31]([C:34]([F:35])([F:37])[F:36])[N:30]=3)=[CH:25][N:24]=2)=[CH:18][N:17]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 67975276HCID 67975276, compound

Product 1

HCID 67973424HCID 67973424, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60%, 35 mg) was added to an N,N-dimethylformamide (3 mL) solution containing methyl 2,2-dimethyl-3-[(4-methyl-5-{5-[5-(trifluoromethyl)-1H-imidazol-2-yl]pyrazin-2-yl}pyridin-2-yl)oxy]propanoate (320 mg) at 0° C., and the resulting mixture was stirred at the same temperature for 1 hour. To the mixture was added 2-(trimethylsilyl)ethoxymethyl chloride (195 μL), a temperature of the mixture was raised to room temperature and the mixture was stirred for 1 hour. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and then with a saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10 to 80:20) to obtain a mixture (324 mg) of methyl 2,2-dimethyl-3-[(4-methyl-5-{5-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]pyrazin-2-yl}pyridin-2-yl)oxy]propanoate and methyl 2,2-dimethyl-3-[(4-methyl-5-{5-[5-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]-pyrazin-2-yl}pyridin-2-yl)oxy]propanoate.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialwith a saturated brine, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10 to 80:20)

Sources & evidence

ORD record
ord-cb0cfdf6a6a747869de82dae345a1e99
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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