Fumaric Acid → 5-[2-(1-azabicyclo[2.2.2]oct-3-yloxy)pyrimidin-5-yl]-2-methylaniline Fumarate

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Reaction Steps

The product of Example 23A (45 mg, 0.14 mmol) in ethyl acetate/ethanol (1:1, 3 mL) was treated with fumaric acid (23 mg, 0.2 mmol) at ambient temperature for 10 hours. The title compound was obtained as a solid (50 mg, yield, 78%). 1H NMR (300 MHz, MeOH-d4) δ 1.85-2.24 (m, 6H), 2.30-2.44 (m, 1H), 2.55-2.62 (m, 1H), 3.23-3.46 (m, 5H), 3.82-3.92 (m, 1H), 5.36-5.44 (m, 1H), 6.69 (s, 2H), 6.87 (dd, J=2.0, 7.8 Hz, 1H), 6.96 (d, J=1.7 Hz, 1H), 7.12 (d, J=8.1 Hz, 1H), 8.78 (s, 2H). ppm. MS (DCl/NH3) m/z 311 (M+H)+. Anal. Calculated for C18H22N4O.1.15C4H4O4: C, 61.15; H, 6.04; N, 12.62. Found: C, 61.14; H, 6.08; N, 12.38.

Provenance & Evidence