3-(4-Chloro-3-methylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-amine → N-[3-(4-chloro-3-methylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl]-2-(cyclopentyloxy)acetamide

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Reaction Steps

The product from Example 133C (1.0 mL of solution in CH2Cl2) was added to a stirring solution of the product from Example 47C (51 mg, 0.178 mmol) in pyridine (1.4 mL). The reaction mixture was stirred at room temperature for 2 hours, and then quenched by addition of MeOH (0.5 mL). After 30 min, concentrated NH4OH (0.2 mL) was added, and the mixture was stirred at room temperature for 12 hours, and then concentrated under vacuum. The residue was purified by flash chromatography (silica gel, eluted with hexanes-EtOAc, 70:30-0:100) to provide the title compound. 1H NMR (300 MHz, CD3OD) δ ppm 1.52-1.81 (m, 8H) 2.42 (s, 3H) 2.56 (s, 3H) 2.73 (d, J=1.0 Hz, 3H) 4.05-4.12 (m, 1H) 4.09 (s, 2H) 6.86-6.89 (q, J=1.0 Hz, 1H) 7.40 (d, J=8.5 Hz, 1H) 7.54 (dd, J=8.4, 1.9 Hz, 1H) 7.65 (d, J=1.9 Hz, 1H); MS (DCI/NH3) m/z 413/415 (M+H)+.

Provenance & Evidence