Water → HCID 66877930, compound

(Step 4) To a solution of 1-[5-bromo-2-(methylsulfanyl)phenyl]methanamine hydrochloride obtained in Step 3 (6.25 g) and triethylamine (4.72 g) in tetrahydrofuran (150 ml) was added di-t-butyl dicarbonate (7.62 g) at room temperature. The mixture was stirred at the same temperature for 14 hr, treated with water, and extracted with ethyl acetate. The extract was washed successively with 1N hydrochloric acid and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in ethyl acetate (200 ml), and m-chloroperbenzoic acid (14.4 g, containing water: Wako Pure Chemical Industries, Ltd.) was added at room temperature. The mixture was stirred at the same temperature for 4 hr, and treated with aqueous sodium hydrogen carbonate solution. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=2:1). The obtained residue was dissolved in methanol (100 ml), 4N hydrogen chloride-ethyl acetate solution (15 ml) was added, and the mixture was stirred at 60° C. for 1 hr, and concentrated under reduced pressure to give crystals. The obtained crystals were washed with ethyl acetate to give 1-[5-bromo-2-(methylsulfonyl)phenyl]methanamine hydrochloride (5.85 g) as a solid.

1. extractionextracted with ethyl acetate
2. washThe extract was washed successively with 1N hydrochloric acid and saturated brine
3. dry with materialdried over magnesium sulfate
4. customThe solvent was evaporated under reduced pressure
5. dissolutionThe obtained residue was dissolved in ethyl acetate (200 ml)
6. additionm-chloroperbenzoic acid (14.4 g, containing water: Wako Pure Chemical Industries, Ltd.) was added at room temperature
7. stirringThe mixture was stirred at the same temperature for 4 hr
8. additiontreated with aqueous sodium hydrogen carbonate solution
9. washThe organic layer was washed with saturated brine
10. dry with materialdried over magnesium sulfate
11. customThe solvent was evaporated under reduced pressure
12. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=2:1)
13. dissolutionThe obtained residue was dissolved in methanol (100 ml)
14. addition4N hydrogen chloride-ethyl acetate solution (15 ml) was added
15. stirringthe mixture was stirred at 60° C. for 1 hr
16. concentrationconcentrated under reduced pressure
17. customto give crystals
18. washThe obtained crystals were washed with ethyl acetate

ORD record

ord-632f8e7d9dd54094b9460bc202705207

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985862B2