Dimethylformamide → HCID 86617930, compound

HRID 1161588Notes

Reaction equation

HRID 1161588 reaction equation
CN(C=O)C.[CH3:6][O:7][C:8](=[O:38])[N:9]=[C:10]([S:36][CH3:37])[C:11]([C:25]1[CH:30]=[C:29]([O:31][CH2:32][CH3:33])[CH:28]=[C:27]([OH:34])[C:26]=1[F:35])=[N:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]=[C:22]([CH3:24])[O:21][N:20]=2)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:46][CH2:47][O:48][CH:49]1[CH2:54][CH2:53][CH2:52][CH2:51][O:50]1>O>[CH3:6][O:7][C:8](=[O:38])[N:9]=[C:10]([S:36][CH3:37])[C:11]([C:25]1[CH:30]=[C:29]([O:31][CH2:32][CH3:33])[CH:28]=[C:27]([O:34][CH2:46][CH2:47][O:48][CH:49]2[CH2:54][CH2:53][CH2:52][CH2:51][O:50]2)[C:26]=1[F:35])=[N:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]=[C:22]([CH3:24])[O:21][N:20]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 72312778HCID 72312778, compound

Product 1

HCID 86617930HCID 86617930, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2 ml of a DMF solution containing 75 mg of {2-(5-ethoxy-2-fluoro-3-hydroxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester, 100 mg of potassium carbonate and 0.1 ml of 2-(2-bromoethoxy)tetrahydro-2H-pyran were added. The resulting mixture was stirred at room temperature for 10 hours, and then water was added thereto. The mixture was extracted with ethyl acetate. The organic layer was washed with water and then dried through PRESEP™. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give {2-{5-ethoxy-2-fluoro-3-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester (51 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. customdried through PRESEP™
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-b94c56efeaee47c8bb2366d6185828c5
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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