1-Chloroethyl chloroformate → HCID 67468519, compound

Temperature

0 °C

To a solution of 2-(I-benzylpiperidin-4-yloxy)-6-(1-(propylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole (1.812 g, 3.54 mmol) in dichloroethane (30 mL) at 0° C. was added 1-chloroethyl carbonochloridate (0.497 mL, 4.60 mmol). Upon completion of addition, the reaction mixture was stirred at 0° C. for 15 min and then heated to reflux, where it stirred for 1 h. At the conclusion of this period, the volatiles were removed under vacuum and the resulting sample was dissolved in MeOH (30 mL) and then heated to reflux, where it stirred for 1 h. After this time, the reaction mixture was cooled to rt and then concentrated under reduced pressure to yield a residue. The residue was diluted with CH2Cl2 and washed with aq K2CO3 (saturated, 10 mL) and brine (10 mL). The organic layer was dried (Na2SO4), filtered, and then concentrated to afford Compound 15A (1.405 g, 3.33 mmol, 94% yield). LC/MS (m/z)=422 (M+H)+.

1. additionUpon completion of addition
2. temperatureheated
3. temperatureto reflux
4. stirringwhere it stirred for 1 h
5. customAt the conclusion of this period, the volatiles were removed under vacuum
6. dissolutionthe resulting sample was dissolved in MeOH (30 mL)
7. temperatureheated
8. temperatureto reflux
9. stirringwhere it stirred for 1 h
10. temperatureAfter this time, the reaction mixture was cooled to rt
11. concentrationconcentrated under reduced pressure
12. customto yield a residue
13. washwashed with aq K2CO3 (saturated, 10 mL) and brine (10 mL)
14. dry with materialThe organic layer was dried (Na2SO4)
15. filtrationfiltered
16. concentrationconcentrated

ORD record

ord-22fa99c149c54e6287a268305bc248dd

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940716B2