4-Methylmorpholine → HCID 59750777, compound

To a dichloromethane solution (6 ml) of the 4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)butylamine hydrochloride (120 mg, 0.303 mmol) obtained in Example 227 were added N-methylmorpholine (250 μl, 2.69 mmol) and 4-chlorobutyric acid chloride (40.7 μl, 0.364 mmol). After stirring at room temperature for 1 hour, the reaction mixture was diluted with dichloromethane, washed successively with a saturated aqueous solution of ammonium chloride, water and brine, dried over magnesium sulfate and then, concentrated. The residue thus obtained was dissolved in tetrahydrofuran (5 ml), followed by the addition of sodium hydride (60% dispersion in mineral oil, 14.2 mg, 0.356 mmol) and N,N-dimethylformamide (2 drops). The resulting mixture was stirred at room temperature for 24 hours. Water was added and the resulting mixture was extracted with ethyl acetate. The extracts were combined, washed with brine, dried over magnesium sulfate and then concentrated. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=1:1 eluate was concentrated, whereby the title compound (105 mg, 0.245 mmol, 82%) was obtained as a colorless oil.

1. washwashed successively with a saturated aqueous solution of ammonium chloride, water and brine
2. dry with materialdried over magnesium sulfate
3. concentrationconcentrated
4. customThe residue thus obtained
5. stirringThe resulting mixture was stirred at room temperature for 24 hours
6. extractionthe resulting mixture was extracted with ethyl acetate
7. washwashed with brine
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated
10. customThe residue thus obtained
11. concentrationethyl acetate=1:1 eluate was concentrated

ORD record

ord-b3c0e86465ac47c9b7ed84919d13482b

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399775B2