Dimethylformamide → HCID 86617929, compound

HRID 1161586Notes

Reaction equation

HRID 1161586 reaction equation
CN(C=O)C.[CH3:6][O:7][C:8](=[O:34])[N:9]=[C:10]([S:32][CH3:33])[C:11](=[N:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[C:25]([F:31])[CH:24]=1)[C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([OH:20])[C:13]=1[F:21].C(=O)([O-])[O-].[K+].[K+].Br[CH2:42][CH2:43][O:44][CH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][O:46]1>O>[CH3:6][O:7][C:8](=[O:34])[N:9]=[C:10]([S:32][CH3:33])[C:11](=[N:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[C:25]([F:31])[CH:24]=1)[C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH2:42][CH2:43][O:44][CH:45]2[CH2:50][CH2:49][CH2:48][CH2:47][O:46]2)[C:13]=1[F:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 72312741HCID 72312741, compound

Product 1

HCID 86617929HCID 86617929, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2 ml of a DMF solution containing 200 mg of [2-(4-cyano-3-fluorophenylimino)-2-(2-fluoro-3-hydroxy-5-methoxyphenyl)-1-methylsulfanylethylidene]carbamic acid methyl ester, 300 mg of potassium carbonate and 0.2 ml of 2-(2-bromoethoxy)tetrahydro-2H-pyran were added. The resulting mixture was stirred at room temperature for 18 hours, and then water was added thereto. The mixture was extracted with ethyl acetate. The organic layer was washed with water and then with 5 saturated brine and dried over anhydrous sodium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give (2-(4-cyano-3-fluorophenylimino)-2-{2-fluoro-5-methoxy-3-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}-1-methylsulfanylethylidene)carbamic acid methyl ester (150 mg) as a yellow oil.

Workup

  1. additionwere added
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialwith 5 saturated brine and dried over anhydrous sodium sulfate
  5. customThe desiccating agent was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-4450c74ef64a43eab6e7da7957325bbd
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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