N-[(3R)-l-azabicyclo [2.2.2] oct-3-yl]-5-amino-l-benzofuran-2-carboxamide
N-[(3R)-l-azabicyclo [2.2.2] oct-3-yl]-5-nitro-l-benzofuran-2-carboxamide (100 mg, 0.32 mmol) is mixed with 2.0 ml (4 mmol) of a 2 M tin added (II) chloride solution in DMF. The mixture is stirred overnight. The reaction mixture is poured into water and made basic with 1 N aqueous sodium hydroxide solution. The aqueous phase is extracted six times with ethyl acetate. The combined organic
Phases are dried over magnesium sulfate and the solvent under reduced pressure on a rotary evaporator enfemt. The crude product is taken up in methanol and with acidic ion exchange resin (Dowex WX2-200) min about 20. shaken. The loaded ion exchanger. Three times with 30 ml of methanol, then with water / methanol 8:2, again with methanol, dichloromethane, and finally washed with methanol The product is eluted with methanol / triethylamine 95:5. The solvent is removed under reduced pressure on a rotary evaporator. 52 mg can be isolated (58% of theory) of the title compound.
1H NMR (400 MHz, methanol-d4): δ = 7.35 (d, IH), 7.32 (s, IH), 6.97 (d, IH), 6.89
(Dd, 3H), 4:24 to 4:18 (m, IH), 3:34 to 3:29 (m, IH), 3.07-2.97 (m, IH), 2.93-2.77 (m, 4H), 2:13 to 2:05 (m, IH) , 1.98-1.86 (m, IH), 1.84-1.75 (m, 2H), 1.63-1.53 (m, IH) ppm.
MS (ESIpos): m / z = 286 (M + H) + (free base)
LC-MS (Method D): R t = 2.02 min, m / z = 286 (M + H) + (free base).
