N,N-Dimethyl-1,3-propanediamine → HCID 19867671, compound

Participants

Reaction Conditions

Reaction Steps

3-Dimethylaminopropylamine (4.1 g) is added at a temperature in the region of 20° C. to a suspension of 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (6.6 g) in anhydrous tetrahydrofuran (100 cc), and the reaction mixture is heated to reflux for 6 hours. After the reaction mixture has been stirred for a further 20 hours at a temperature in the region of 20° C., it is filtered. The isolated solid is washed with ethyl acetate (3×25 cc). The filtrate is washed with distilled water (3×25 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) at 60° C. 1N aqueous hydrochloric acid solution (20 cc) is added to the residue obtained. An insoluble product is separated by filtration, washed with 1N aqueous hydrochloric acid solution (2×5 cc) and then discarded. The aqueous filtrates are combined and alkalinized with a saturated aqueous potassium bicarbonate solution to a pH in the region of 8, and then extracted with ethyl acetate (3×40 cc). The organic phases are combined, dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 60° C. After recrystallization in ethyl acetate, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(3-dimethylaminopropylamino)-1-isoindolinone (3 g), m.p. 143° C., is obtained.

Provenance & Evidence