Acryloyl chloride → N-(3-{[2-({1-[2-(dimethylamino)ethyl]-1H-pyrazol-4-yl}amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy}phenyl)prop-2-enamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(3-aminophenoxy)-N-{1-[2-(dimethylamino)ethyl]-1H-pyrazol-4-yl}-7H-pyrrolo[2,3-d]pyrimidin-2-amine in THF (5 mL) which was cooled to 10° C. was added prop-2-enoyl chloride (47.8 mg, 0.528 mmol) and stirred at 10° C. for 3 hrs. The volatiles were removed in vacuo and the residue purified by HPLC (Phenominex Gemini C18, 21.2×100 mm, 5 μm column using the water/acetonitrile with 10 mM ammonium acetate, with the flow rate 40 mL/min with gradient 55%-67% acetonitrile in 6 min) which was then lyophilized to afford the title compound (28.5 mg, 11% yield) as a tan solid. 1H NMR (600 MHz, DMSO-D6) δ ppm 11.06-11.23 (m, 1H) 9.96-10.08 (m, 1H) 8.56-8.64 (m, 1H) 7.56-7.66 (m, 2H) 7.39-7.47 (m, 2H) 7.30-7.36 (m, 1H) 6.94-7.02 (m, 2H) 6.37-6.47 (m, 1H) 6.18-6.30 (m, 2H) 5.68-5.80 (m, 1H) 3.89-4.04 (m, 2H) 2.57-2.64 (m, 2H) 2.18 (s, 6H). m/z (ESI+) for C22H24N8O2 433.2 (M+H)+.

Provenance & Evidence