1-Methyl-4-(pyrrolidin-2-yl)piperidine → 2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-9-(2-(1-methylpiperidin-4-yl)pyrrolidin-1-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepine

Participants

Reaction Conditions

Reaction Steps

A mixture of 12-chloro-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene from Example 135 (160 mg, 0.480 mmol), TEA (0.50 mL), and 1-methyl-4-(pyrrolidin-2-yl)piperidine (161 mg, 0.960 mmol) in NMP (0.5 mL) was stirred at 150° C. for 24 h under nitrogen atmosphere. The resultant mixture was then purified by reverse phase combiflash eluting with a 0-50% gradient of CH3CN in 0.3% NH4HCO3 to give 106 (66 mg, 60% yield). LCMS (ESI): RT=4.11 min, m/z: 463.3 [M+H+]. 1H NMR (500 MHz, DMSO-d6): δ 9.08 (t, J=10.5 Hz, 1H), 7.90 (t, J=10.5 Hz, 1H), 7.84 (t, J=10 Hz, 1H), 5.98 (t, J=20 Hz, 2H), 4.52-4.47 (m, 4H), 4.10 (s, 1H), 3.45 (d, J=6.5 Hz, 1H), 2.78 (s, 1H), 2.11 (d, J=10 Hz, 3H), 1.93-1.66 (m, 8H), 1.50-1.39 (m, 7H), 1.31-1.27 (m, 3H)

Provenance & Evidence