Pyridine → HCID 67443215, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of tert-butyl 2-(4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-1H-pyrazol-1-yl)ethyl(2-methoxyethyl)carbamate (245, 1.22 g, 2.312 mmol) and pyridine (374 μL, 4.62 mmol) in DMF (30 mL) at 0° C. was added phenyl chloroformate (348 μl, 2.77 mmol) and the reaction mixture was stirred for 30 min. Cyclopropylamine (407 μl, 5.78 mmol) was added at 0° C. and the reaction mixture was heated at 60° C. for an additional 30 min. After cooling to RT, the reaction mixture was quenched by addition of water and a saturated solution of ammonium chloride, and extracted with AcOEt. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by Biotage (SNAP 80 g cartridge; MeOH/DCM: 0/100 to 10/90 over 20 CV). The desired fractions were collected and concentrated to afford the title compound 246 (722 mg, 0.18 mmol, 61% yield) as a yellow solid. MS (m/z): 611.63 (M+H).

Provenance & Evidence