Ammonium Chloride → HCID 90370135, compound

Participants

Reaction Steps

To a mixture of 350 mg of 2-[3-(morpholin-4-ylmethyl)phenyl]-5,6,7,8-tetrahydro-4H-[1]benzothieno[2,3-d][1,3]oxazin-4-one, 150 mg of 2-N,2-N-diethylpyrimidine-2,5-diamine and 5.0 mL of THF was added dropwise 1.0 mL of lithium hexamethyldisilazide (1.0 M in THF) under ice cooling, followed by stirring for 1 hour at the same temperature. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (methanol/chloroform). Ethyl acetate and 0.5 mL of 4.0 M hydrogen chloride/ethyl acetate solution were sequentially added to the residue, followed by stirring for 30 minutes at room temperature. The insoluble material was collected by filtration, thereby obtaining 174 mg of N-[2-(diethylamino)pyrimidin-5-yl]-2-{[3-(morpholin-4-ylmethyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide dihydrochloride.

Provenance & Evidence