Hydrochloric Acid → HCID 86724090, compound

Participants

Reaction Steps

To 4-(2,4-dichlorophenyl)-1,3,6,6-tetramethyl-7,8-dihydro-4H-pyrazolo[3,4-e][1,4]thiazepine (0.12 g, 0.33 mmol, Example #D.4) dissolved in DMF (10 mL), was added NaH (0.133 g, 3.33 mmol, 60% dispersion in mineral oil) and methyl iodide (0.21 mL, 3.33 mmol). The reaction mixture was stirred for about 24 h at rt. To the reaction mixture was added 5% aqueous sodium bicarbonate (30 mL) and ethyl acetate (25 mL). The layers were separated and the organic layer was washed with water (25 mL), dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, ethyl acetate/DCM (1:9 followed by 1:4)), to 4-(2,4-dichlorophenyl)-1,3,6,6,8-pentamethyl-4,7-dihydropyrazolo[3,4-e]thiazepine (0.07 g, 0.189 mmol, 57%), which was dissolved in ethyl acetate and converted into the HCl salt (using 1M HCl/ethanol). The precipitated solid is collected by filtration and washed with a small amount of diethyl ether to afford 4-(2,4-dichlorophenyl)-1,3,6,6,8-pentamethyl-4,7-dihydropyrazolo[3,4-e][1,4]thiazepine hydrochloride (0.053 g, 0.13 mmol, 39%) as an off white solid. LC-MS (Table 1, Method d) Rr=3.05 min, m/z 370 (M+H)+

Provenance & Evidence