Water → HCID 10125856, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[2-(cyclopropylamino)-4-pyrimidinyl]pyrazolo[1,5-b]pyridazin-6-yl trifluoromethanesulfonate (107 mg, 0.268 mmol) in DMF (2 mL) was added DIEA (0.093 mL, 0.536 mmol) and cyclopentylamine (0.026 mL, 0.268 mmol). The reaction mixture was heated at an oil bath temperature of 50° C. for about 1 hour at which point N-phenyltrifluoromethylsulfonimide (95 mg, 0.268 mmol) was added followed by an additional portion (equivalent) of cyclopentylamine and DIEA This was repeated two more times. The mixture was cooled to RT and water (20 mL) was added. The aqueous layer was washed with EtOAc (3×50 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo and purified by silica-gel column 0.15 chromatography (gradient, 0-10% MeOH in CH2Cl2). The residue was suspended in EtOAc and triturated with hexanes to give the title compound as a yellow solid (26 mg, 29%). 1H-NMR (300 MHz, CDCl3) 8.71 (d, 1H, J=9.5 Hz), 8.17 (s, 2H), 6.89 (d, 1H, J=5.7 Hz), 6.55 (d, 1H, J=9.3 Hz), 5.92 (bs, 1H), 4.43 (m, 1H), 4.30 (m, 1H), 2.84 (m, 1H), 2.16 (m, 2H), 1.71 (m, 4H), 1.50 (m, 2H), 0.87 (m, 2H), 0.66 (m, 2H); MS (APCI) (M+H)+ 336.

Provenance & Evidence