Hydrazine → 3-Amino-N-[4-(3-aminocyclohexyl)pyridin-3-yl]-7-ethylquinoline-2-carboxamide

Participants

Reaction Steps

A mixture of 3-amino-7-ethylquinoline-2-carboxylic acid (0.040 g, 0.18 mmol), 2-[3-(3-aminopyridin-4-yl)cyclohexyl]-1H-isoindole-1,3(2H)-dione (0.055 g, 0.17 mmol), HATU (0.22 g, 0.58 mmol), DMF (0.65 mL) and DIPEA (0.076 g, 0.59 mmol) was stirred at room temperature for 16 h. Aq. NaOH (1 M) was added to the reaction mixture, and a precipitate formed, which was collected by vacuum filtration. The collected solid was washed with 1 M NaOH, followed by water and dried under vacuum to afford an intermediate. The intermediate was dissolved in DMF (0.15 mL) and hydrazine (0.15 mL) was added. The resulting reaction mixture was stirred at room temperature for 16 h, diluted with MeOH, filtered and purified by preparative LC MS (XBridge™ preparative C18 5 μm 30×10 mm OBD™ column, flow rate 60 mL/min., eluting with a gradient of MeCN and water with 0.15% NH4OH) to give title compound. LCMS calc. for C23H28N5O (M+H)+: m/z=390.2. Found: 390.1.

Provenance & Evidence