1,4-Dioxane → {2-ethyl-8-fluoro-3-[4-(morpholine-4-sulfonyl)benzyl]-4-oxo-1,4-dihydroquinolin-5-yloxy}acetic Acid Methyl Ester

HRID 2266599Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([NH2:13])[CH:7]=1.C[O:16][C:17](=O)[CH:18]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)(=[O:32])=[O:31])=[CH:26][CH:25]=1)[C:19](=O)[CH2:20][CH3:21].O1CCOCC1>O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:7]=1[C:17](=[O:16])[C:18]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([S:30]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)(=[O:32])=[O:31])=[CH:28][CH:29]=1)=[C:19]([CH2:20][CH3:21])[NH:13]2

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of (3-amino-4-fluorophenoxy)acetic acid methyl ester (0.22 g), 2-[4-(morpholine-4-sulfonyl)benzyl]-3-oxopentanoic acid methyl ester (0.41 g), polyphosphoric acid (1 g) and dioxane (20 mL) was heated at 130° C. for 18 hours. The mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate, dichloromethane and methanol (1:4:0 to 1:1:0 to 0:9:1 by volume) to afford title compound, 0.14 g.

Workup

temperatureThe mixture was cooled to room temperature
extractionextracted with ethyl acetate
dry with materialThe combined extracts were dried over magnesium sulfate
customthe solvent removed under reduced pressure
customThe residue was purified by column chromatography on silica gel
washeluting with a mixture of ethyl acetate, dichloromethane and methanol (1:4:0 to 1:1:0 to 0:9:1 by volume)

Sources & evidence

ORD record: ord-faa5e49a3e7a4a149e18c721f7263a20
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

Loading…