1-Propanol → HCID 57699132, compound

Sodium hydride (12 mg) was added, while cooled with ice, to a dimethylformamide (1.2 ml) solution of the 4-chloro-N-{(1R)-1-[4-ethyl-5-(methylsulfonyl)-4H-1,2,4-triazol-3-yl]ethyl}benzenesulfonamide (Compound 182) (47 mg) obtained in Example 5 and n-propanol (0.027 ml). The mixture was stirred for 30 minutes at room temperature, and then stirred for 2 hours at 100° C. After the reaction mixture was cooled to room temperature, it was added to a saturated aqueous solution (5 ml) of ammonium chloride. The mixture was extracted with ethyl acetate (20 ml×2) and washed with a saturated aqueous solution (20 ml) of sodium chloride. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel flash column chromatography using a solvent mixture of methanol and chloroform to obtain Compound 183 (35 mg).

1. stirringstirred for 2 hours at 100° C
2. temperatureAfter the reaction mixture was cooled to room temperature
3. extractionThe mixture was extracted with ethyl acetate (20 ml×2)
4. washwashed with a saturated aqueous solution (20 ml) of sodium chloride
5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
6. distillationthe solvent was distilled off under reduced pressure
7. customThe resulting residue was purified by silica gel flash column chromatography
8. additiona solvent mixture of methanol and chloroform

ORD record

ord-3348ace328074b2d8ae8725c4283d80c

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022225B2