Acetyl chloride → (R)-N-ethyl-N-(6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

(R)-1-(3-(Ethylamino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (Example 2, Step 2; 680 mg, 1.198 mmol) was dissolved in DCM (20 mL), charged with DIEA (0.42 mL, 2.396 mmol), and cooled to 0° C. Acetyl chloride (0.095 mL, 1.318 mmol) was added drop-wise and the reaction was warmed to room temperature and stirred for 1 h. The reaction was charged with TFA (2.3 mL, 30.0 mmol) and triethylsilane (0.20 mL, 1.198 mmol) and stirred for 1 h at room temperature. The solvents were removed in vacuo and the residue was treated with DCM (3 mL) and triethylamine (1 mL) and stirred for 15 min. The residue was purified by flash chromatography (2-10% MeOH/DCM w/NH3) to afford (R)—N-ethyl-N-(6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide. MS ESI calc'd. for C19H22N6O2 [M+1]+ 366. found 366.

Provenance & Evidence