Dimethylformamide → HCID 86617931, compound

HRID 1161589Notes

Reaction equation

HRID 1161589 reaction equation
CN(C=O)C.[CH3:6][O:7][C:8](=[O:37])[N:9]=[C:10]([S:35][CH3:36])[C:11]([C:25]1[CH:30]=[C:29]([OH:31])[CH:28]=[C:27]([O:32][CH2:33][CH3:34])[CH:26]=1)=[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[CH2:45][CH2:46][O:47][CH:48]1[CH2:53][CH2:52][CH2:51][CH2:50][O:49]1>O>[CH3:6][O:7][C:8](=[O:37])[N:9]=[C:10]([S:35][CH3:36])[C:11]([C:25]1[CH:30]=[C:29]([O:31][CH2:45][CH2:46][O:47][CH:48]2[CH2:53][CH2:52][CH2:51][CH2:50][O:49]2)[CH:28]=[C:27]([O:32][CH2:33][CH3:34])[CH:26]=1)=[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 72312784HCID 72312784, compound

Product 1

HCID 86617931HCID 86617931, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1 ml of a DMF solution containing 80 mg of {2-(3-ethoxy-5-hydroxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester (Example (78a)), 200 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 overnight, and then water was added thereto. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and then concentrated. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give {2-{3-ethoxy-5-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester (76 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 and saturated brine
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-a5567f7c8f104cf99eefd4c7f4d830cb
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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