Water → HCID 58452882, compound

HRID 70592Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH:9][CH2:10][CH3:11])[CH3:8].CC1C=CC(S(O[CH2:23][CH2:24][CH2:25][S:26][C:27]2[CH:32]=[CH:31][C:30](/[C:33](/[C:40]3[NH:41][C:42](=[O:47])[C:43]([CH3:46])=[CH:44][CH:45]=3)=[CH:34]\[CH:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)=[CH:29][C:28]=2[Cl:48])(=O)=O)=CC=1.O>C(#N)C>[Cl:48][C:28]1[CH:29]=[C:30](/[C:33](/[C:40]2[NH:41][C:42](=[O:47])[C:43]([CH3:46])=[CH:44][CH:45]=2)=[CH:34]\[CH:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:31]=[CH:32][C:27]=1[S:26][CH2:25][CH2:24][CH2:23][N:9]([CH2:10][CH3:11])[CH2:7][CH3:8]

Participants

Conditions

Temperature: 90 °C

Procedure

Potassium carbonate (290 mg) and diethylamine (219 μL) were sequentially added to a solution of 3-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-methyl-6-oxo-1,6-dihydropyridin-2-yl)ethenyl]phenyl}sulfanyl)propyl 4-methylbenzenesulfonate (33 mg) in acetonitrile (3 mL), and the mixture was stirred at 90° C. for two hours. The reaction solution was poured into water, followed by extraction with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1) to give the title compound (18 mg, 66%) as a colorless amorphous.

Workup

extractionfollowed by extraction with chloroform
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was then evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1)

Sources & evidence

ORD record: ord-0872360e61274ce2ae560dd1bd10dfcd
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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