Sodium Hydroxide → HCID 68674708, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 25.0 g of tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(1-(2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate in 50 mL of water, 18 mL of concentrated hydrochloric acid was added dropwise at 28 to 39° C. The reaction mixture was stirred for 3 hours and 30 minutes at 40 to 50° C., cooled to room temperature, added with 17 mL of a 20% sodium hydroxide aqueous solution and 25 mL of water and heated to 60° C. The mixture was adjusted to pH 3 with concentrated hydrochloric acid and 25 mL of water was added thereto. Insoluble matter was filtered out at 50° C. and the filter residue was washed using 25 mL of water. The filtrate and the wash liquid were combined and heated to 40° C., added with 13.5 mL of a 20% sodium hydroxide aqueous solution, 150 mL of 2-butanone and 25 mL of water, and refluxed with heating to dissolve the solid matter. The reaction mixture was cooled to 10° C. and the solid product obtained by filtration was washed with water to give 19.3 g of 1-(2-(4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)piperidin-1-yl)ethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one monohydrate as a light yellow solid.

Provenance & Evidence