Water → (2-{3,4-Dimethoxy-5-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]-1-methylsulfanylethylidene)carbamic acid methyl ester

HRID 1161509Notes

Reaction equation

HRID 1161509 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1.[CH3:17][O:18][C:19](=[O:49])[N:20]=[C:21]([S:47][CH3:48])[C:22]([C:36]1[CH:41]=[C:40]([O:42][CH3:43])[C:39]([O:44][CH3:45])=[C:38]([OH:46])[CH:37]=1)=[N:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:34]=[C:33]([CH3:35])[O:32][N:31]=2)=[CH:26][CH:25]=1.O>CN(C=O)C.C(OCC)(=O)C>[CH3:17][O:18][C:19](=[O:49])[N:20]=[C:21]([S:47][CH3:48])[CH:22]([C:36]1[CH:37]=[C:38]([O:46][CH2:8][CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[C:39]([O:44][CH3:45])=[C:40]([O:42][CH3:43])[CH:41]=1)[NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:34]=[C:33]([CH3:35])[O:32][N:31]=2)=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 72312728{2-(3-Hydroxy-4,5-dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

Product 1

HCID 68423102(2-{3,4-Dimethoxy-5-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]-1-methylsulfanylethylidene)carbamic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 300 mg of potassium carbonate and 0.1 ml of 2-(2-bromoethoxy)tetrahydro-2H-pyran to a solution of 100 mg of {2-(3-hydroxy-4,5-dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester in 1 ml of DMF, the mixture was stirred at room temperature for 20 hours. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine in that order, and dried through PRESEP™. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give (2-{3,4-dimethoxy-5-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]-1-methylsulfanylethylidene)carbamic acid methyl ester (80 mg) as a yellow oil.

Workup

  1. washThe organic layer was washed with water and saturated brine in that order
  2. customdried through PRESEP™
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-682588e54a0c4389a89ffb62d5aa1575
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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