Triethylamine → HCID 68183091, compound

Temperature

0 °C

To a solution of 2-(morpholin-4-yl)-5,6-dihydro-4H-[1,3]thiazolo[5,4-c]azepin-4-one (3.41 g, 13.6 mmol) in DCM (42.0 mL) at 0° C. was added triethylamine (1.02 mL, 7.33 mmol), then a solution of bromine (1.15 mL, 22.4 mmol) in DCM (21.0 mL) was added dropwise and the reaction mixture was stirred at 0° C. for 3 hours. The solvent was evaporated and the residue was dissolved in benzene (80.0 mL) then added 1,8-diazabicyclo[5.4.0]undec-7-ene (6.09 mL, 40.7 mmol) and the solution was stirred at room temperature for 16 hours. The reaction mixture was diluted with EA and water, and a precipitate formed which was filtered and dried to give the product (2.90 g). In order to obtain additional product the layers were separated and the aqueous layer was extracted twice more with EA. The combined organic layer was then washed with brine then dried over anhydrous sodium sulfate and concentrated. The residue was adsorbed onto silica gel then purified using column chromatography on silica gel (40 gr Analogix column, gradient DCM to 5% MeOH in DCM over 15 minutes) to give 0.223 g additional product (total product: 3.02 g, 67%). LCMS: (AA) ES+ 331, 333. 1H NMR (300 MHz, d6-DMSO) δ: 8.14-7.89 (m, 1H), 6.69 (t, J=7.3 Hz, 1H), 3.81-3.62 (m, 4H), 3.55-3.38 (m, 6H).

1. customThe solvent was evaporated
2. dissolutionthe residue was dissolved in benzene (80.0 mL)
3. customa precipitate formed which
4. filtrationwas filtered
5. customdried

ORD record

ord-be1d9446719b4007a4fbb7bafb8abc49

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765746B2