Ethyl Acetate → HCID 86637605, compound

HRID 1966295Notes

Reaction equation

Cl[CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[O:20][CH3:21])=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:24])=[CH:6][C:7]([CH3:23])([CH3:22])[NH:8]2.[CH3:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[S:31])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[C:3]([CH2:2][O:32][C:30](=[S:31])[C:29]3[CH:33]=[CH:34][C:26]([CH3:25])=[CH:27][CH:28]=3)=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7]([CH3:22])([CH3:23])[CH:6]=[C:5]3[CH3:24])=[C:14]([O:20][CH3:21])[CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

5-Chloromethyl-6-(4-fluoro-2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 5-2, 50.0 mg, 0.145 mmol), 4-methylthiobenzoic acid (73.2 mg, 0.435 mmol), and potassium carbonate (80.2 mg, 0.580 mmol) were suspended in anhydrous N,N-dimethylformamide (1 mL), and the reaction mixture was stirred at 80° C. for 2.5 hours. Ethyl acetate (100 mL) was added to the reaction mixture, and the whole was washed with water (100 mL) and saturated brine (100 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (32.4 mg) as a colorless amorphous product. (Yield 47%)

Workup

washthe whole was washed with water (100 mL) and saturated brine (100 mL) successively
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-241c61b20d7744e388a9eebd7f25b276
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420635B2

Reaction notes

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