Diisopropylethylamine → (S)-N-(1-{7-Fluoro-8-methyl-2-[4-(pyridin-2-yl)piperazin-1-yl]quinolin-3-yl}ethyl)pyrido[3,2-d]pyrimidin-4-amine

Participants

Reaction Steps

Following the procedure described for Intermediate 13, Intermediate 14 (530 mg, 1.1 mmol) and TFA (3 mL) in DCM (6 mL) afforded (S)-1-{7-fluoro-8-methyl-2-[4-(pyridin-2-yl)piperazin-1-yl]quinolin-3-yl}ethanamine as a white foam, which was used in the next step without any further purification. Following the procedure described for Example 5, (S)-1-{7-fluoro-8-methyl-2-[4-(pyridin-2-yl)piperazin-1-yl]quinolin-3-yl}ethanamine (60 mg, 0.16 mmol), 4-chloropyrido[3,2-d]pyrimidine (33 mg, 0.19 mmol) and DIPEA (0.14 mL, 0.8 mmol) in NMP (1.2 mL) afforded the title compound (46 mg, 58%) as a beige solid. δH (DMSO-d6) 8.94-8.89 (2H, m), 8.56 (1H, s), 8.52 (1H, s), 8.20-8.16 (2H, m), 7.91 (1H, dd, J 8.5, 4.3 Hz), 7.74 (1H, dd, J 8.9, 6.3 Hz), 7.65-7.55 (1H, m), 7.32 (1H, t, J 9.1 Hz), 6.96 (1H, d, J 8.6 Hz), 6.71 (1H, dd, J 7.1, 4.9 Hz), 5.95 (1H, m), 3.87-3.69 (6H, m), 3.33-3.23 (2H, m), 2.58 (3H, s), 1.68 (3H, d, J 6.7 Hz). LCMS (ES+) 495 (M+H)+, RT 3.09 minutes (Method 4).

Provenance & Evidence