1-Methylpiperazine → HCID 68525679, compound

Participants

Reaction Conditions

Reaction Steps

The product from Example 19A (26 mg, 0.11 mmol) was dissolved in dichloromethane (2 mL), treated with 70% 3-chloroperoxybenzoic acid (83 mg, 0.34 mmol), stirred at room temperature for 1 hour, treated with sodium sulfite solution, treated with sodium bicarbonate solution, and extracted with dichloromethane (2×). The combined dichloromethane layers were dried (magnesium sulfate), filtered, concentrated and chromatographed using ethyl acetate in dichloromethane to provide the sulfone intermediate, 4-(methylsulfonyl)-5,6-dihydrofuro[2,3-h]quinazolin-2-amine. This sulfone intermediate was treated with excess 1-methylpiperazine (110 mg, 1.1 mmol) in 2-methoxyethanol (1 mL) heated to 110° C. over night. The reaction mixture was cooled and partitioned between 1 M sodium hydroxide and dichloromethane. The layers were separated and the aqueous layer was extracted with dichloromethane (2×). The combined dichloromethane layers were dried (magnesium sulfate), filtered, concentrated and chromatographed (2, 3.5 and 5% (9:1 methanol:concentrated ammonium hydroxide) in dichloromethane) to provide the title compound: 1H NMR (300 MHz, CDCl3) δ 2.36 (s, 3H), 2.55 (t, J=4.7 Hz, 4H), 2.81 (m, 2H), 2.93 (m, 2H), 3.33 (t, J=4.7 Hz, 4H), 4.80 (br s, 2H), 7.13 (d, J=5.1 Hz, 1H), 7.53 (d, J=5.1 Hz, 1H); MS (DCI/NH3) m/z 286 (M+H)+.

Provenance & Evidence