9-Bromo-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine → HCID 68313219, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 9-bromo-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (200 mg, 0.516 mmol), 4-(pyrrolidin-2-yl)-1-(tetrahydro-2H-pyran-4-yl)piperidine hydrochloride (354 mg, 1.29 mmol), Pd(PtBu3)2 (20 mg, 0.04 mmol), Na2OtBu (148 mg, 1.55 mmol) in toluene (5.0 ml) in a seal tube was degassed with N2 for three times. The mixture was stirred at 110° C. for 120 min. The solid was filtered through Celite. The filtrate was concentrated to give the crude product, which was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/1% formic acid, 17 min) to give racemic 254 (13 mg, 4.6% yield). LCMS (ESI): RT=2.00 min, m/z: 546.4 [M+H+]. 1H NMR (500 MHz, CDCl3): δ 8.33 (d, J=8.5 Hz, 1H), 7.53 (s, 1H), 6.47 (dd, J=9.5 Hz, 2.5 Hz, 1H), 6.18 (d, J=2.5 Hz, 1H), 5.95-5.92 (m, 1H), 4.48-4.36 (m, 4H), 4.05 (d, J=8.5 Hz, 1H), 3.85-3.75 (m, 1H), 3.41-3.24 (m, 6H), 2.41 (s, 4H), 2.02-1.74 (m, 14H), 1.56 (d, J=6.5 Hz, 7H)

Provenance & Evidence