Dimethylformamide → HCID 58964948, compound

HRID 15055Notes

Reaction equation

[C:1](=[O:4])([O-])[O-].[K+].[K+].[C:7]1([CH3:18])[CH:12]=[CH:11][C:10](S(OC)(=O)=O)=[CH:9][CH:8]=1.[CH3:19]N(C=O)C.[N:24]1([CH2:29][CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([N:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]3=[O:44])=[CH:34][CH:33]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1>C(OCC)(=O)C>[CH3:1][O:4][C:10]1[CH:9]=[CH:8][C:7](/[CH:18]=[CH:19]/[C:41]2[CH:42]=[CH:43][N:38]([C:35]3[CH:36]=[CH:37][C:32]([O:31][CH2:30][CH2:29][N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[CH:33][CH:34]=3)[C:39](=[O:44])[CH:40]=2)=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium carbonate (11 mg, 0.08 mmol) and methyl p-toluenesulfonate (6 mg, 0.03 mmol) were added to DMF (2 mL) solution of 4-[(E)-2-4-hydroxyphenyl)vinyl]-1-{4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-1H-pyridin-2-one (11 mg, 0.03 mmol), and stirred for a day and night at 80° C. Ethyl acetate was added to the reaction liquid, followed by washing with water and saturated brine and drying over anhydrous sodium sulfate. Concentrating the reaction liquid under reduced pressure, the residue was purified on silica gel column chromatography (C-300; methanol:chloroform=1:20-1:10) to provide the title compound (6 mg, 53%) as a white solid.

Workup

washby washing with water and saturated brine
dry with materialdrying over anhydrous sodium sulfate
concentrationConcentrating
customthe reaction liquid under reduced pressure
customthe residue was purified on silica gel column chromatography (C-300; methanol:chloroform=1:20-1:10)

Sources & evidence

ORD record: ord-f177d71729334e70bce27de2868c1f16
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732456B2

Reaction notes

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