Cyclohexanone → 6-chloro-N-(4-{[4-(cyclohexylamino)cyclohexyl]methyl}cyclohexyl)-4-(5-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-amine

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Reaction Steps

A suspension of Example 237 (80.0 mg, 0.171 mmol) in MeOH (3 mL) was treated with cyclohexanone (0.035 mL, 0.342 mmol). After 30 minutes, sodium cyanoborohydride (21.5 mg, 0.342 mmol) and zinc chloride (0.699 mg, 5.13 μmol) were added. The reaction was stirred at room temperature overnight. The mixture was concentrated. The residue was treated with sat. NaHCO3 and extracted with EtOAc (2×). The combined organic layers were dried and purified by reverse-phase HPLC as described in Example 56 to give the title compound (32.4 mg) as trifluoroacetic acid salts. 1H NMR (400 MHz, CD3OD) ppm 0.96-1.48 (m, 15H), 1.59-1.96 (m, 10H), 2.01-2.17 (m, 5H), 3.12-3.23 (m, 2H), 3.70 (m, 1H), 3.96 (s, 3H), 6.84-7.01 (m, 2H), 7.93 (m, 1H), 7.99 (s, 1H), 8.10 (s, 1H). MS (DCI+) m/z 550.4 (M+H)+.

Provenance & Evidence