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

Participants

Reaction Steps

A mixture of Example 149e (0.634 g, 2.16 mmol) and 4,4′-methylenedicyclohexanamine (2.267 g, 10.78 mmol) was heated at 155° C. for 90 minutes and cooled. While still warm, the slurry was treated with water and extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered, concentrated, and purified on a 28 g Biotage KP-NH column using the ISCO Companion flash system eluting with MeOH/EtOAc (3:97 to 5:95) to give 593 mg of the title compound. 55 mg of this material was further purified by reverse-phase HPLC as described in Example 56 to give 17 mg of the title compound as trifluoroacetic acid salts. 1H NMR (400 MHz, CD3OD) ppm 1.02-1.45 (m, 9H), 1.57-1.92 (m, 9H), 1.99-2.18 (m, 2H), 3.02 (m, 1H), 3.70 (m, 1H), 3.95 (s, 3H), 6.72-6.92 (m, 2H), 7.80-7.91 (m, 2H), 8.06 (s, 1H). MS (DCI+) m/z 468.3 (M+H)+.

Provenance & Evidence