3-Cyclopentylpropionyl chloride → 3-cyclopentyl-N-(3-isopropylpyrazolo[1,5-a]pyrimidin-2-yl)propanamide

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Reaction Steps

A solution of 3-cyclopentylpropionyl chloride (0.048 mL, 0.31 mmol) in CH2Cl2 (0.2 mL) was added to a stirring solution of the product from Example 112C (35 mg, 0.20 mmol) in pyridine (1.2 mL) in a 4 mL vial. The yellow solution was stirred at room temperature for 3 hours, and then concentrated under vacuum. The residue was dissolved in CH2Cl2 (3 mL) and concentrated under vacuum (repeated three times) to remove excess pyridine. The off-white solid residue was crystallized from 60% ethanol-water (8 mL) to provide the title compound. 1H NMR (300 MHz, CD3OD) δ ppm 1.10-1.27 (m, 2H) 1.41 (d, J=7.1 Hz, 6H) 1.48-1.98 (m, 9H) 2.47 (t, J=7.6 Hz, 2H) 3.01-3.22 (m, 1H) 6.91 (dd, J=7.1, 4.1 Hz, 1H) 8.42 (dd, J=4.1, 2.0 Hz, 1H) 8.70 (dd, J=7.1, 1.7 Hz, 1H); MS (ESI) m/z 301 (M+H)+; Anal. Calculated for C17H24N4O: C, 67.97; H, 8.05; N, 18.65. Found: C, 68.03; H, 8.03; N, 18.60.

Provenance & Evidence