1-Tert-butyl-4-hydrazinylpiperidine hydrochloride → 9-(1-(1-tert-butylpiperidin-4-yl)-1H-1,2,4-triazol-5-yl)-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

Participants

Reaction Conditions

Reaction Steps

A mixture of N-[(1E)-(dimethylamino)methylidene]-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene-12-carboxamide (50 mg, 0.12 mmol) and 1-tert-butyl-4-hydrazinylpiperidine hydrochloride (51 mg, 0.25 mmol) in AcOH (10 mL) was heated at 100° C. for 1 h. The solvent was removed under reduce pressure, and the residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to afford 258 (30 mg, 48% yield) as a white solid. LCMS (ESI): RT=4.77 min, m/z: 516.4 [M+H+]. 1H NMR (500 MHz, DMSO-d6) δ 8.58-8.57 (d, J=8.0 Hz, 1H), 8.07 (s, 1H), 7.99 (s, 1H), 7.43-7.41 (dd, J=8.5, 2.0 Hz, 1H), 7.30 (d, J=1.5 Hz, 1H), 5.86 (m, 1H), 4.58 (s, 4H), 4.29 (m, 1H), 3.08-3.06 (m, 2H), 2.26 (s, 3H), 2.13-2.02 (m, 6H), 1.48-1.47 (d, J=6.5 Hz, 6H), 1.02 (s, 9H)

Provenance & Evidence