D-Lactic Acid → HCID 86690698, compound

Participants

Reaction Steps

To a solution of 8-chloro-1-(piperidin-4-yl)-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridine hydrochloride (600 mg, 1.85 mmol) in DMF (15 mL) was added (R)-2-hydroxypropanoic acid (540 mg, 1.85 mmol), HATU (850 mg, 2.21 mmol) and DIEA (0.8 mL, 3.70 mmol). The mixture was stirred at room temperature overnight. Another 3 eq of HATU and 2 eq of DIEA were added because the reaction did not go to completion as shown by HPLC-MS. The mixture was stirred for another 30 min, and was then diluted with water. The resulting mixture was extracted with ethyl acetate twice. The combined organic layers were dried over anhydrous Na2SO4, and concentrated to give the crude product, which was subsequently purified by chromatography on silica gel using EtOAc:PE as eluent to afford (R)-1-(4-(8-chloro-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridin-1-yl)piperidin-1-yl)-2-hydroxypropan-1-one as a yellow solid (136 mg, yield 20.4%). MS (m/z): 361 (M+H)+.

Provenance & Evidence