3-cyclopropylpropanoyl Chloride → N-[3-(4-chloro-3-methylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl]-3-cyclopropylpropanamide

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Reaction Steps

A solution of the product from Example 114D (40.9 mg, 0.308 mmol) in CH2Cl2 (2 mL) was added to a stirring solution of the product from Example 47C (49.5 mg, 0.173 mmol) in pyridine (1.5 mL) at room temperature. The solution was stirred at room temperature for 1 hour, and then concentrated under vacuum. Methanol (2 mL) was added, and the mixture was concentrated under vacuum. The residue was crystallized from 60% EtOH-water (8 mL) to provide the title compound (52 mg). 1H NMR (300 MHz, CD3OD) δ ppm 0.01-0.14 (m, 2H) 0.37-0.52 (m, 2H) 0.66-0.82 (m, 1H) 1.48-1.65 (m, 2H) 2.40 (s, 3H) 2.50 (t, J=7.0 Hz, 2H) 2.57 (s, 3H) 2.72 (s, 3H) 6.88 (s, 1H) 7.37 (d, J=8.1 Hz, 1H) 7.55 (dd, J=8.6, 1.5 Hz, 1H) 7.65 (d, J=1.0 Hz, 1H)); MS (ESI) m/z 383/385 (M+H)+; Anal. Calculated for C21H23N4OCl: C, 65.87; H, 6.05; N, 14.63. Found: C, 65.56; H, 6.08; N, 14.63.

Provenance & Evidence