Sulfuric acid magnesium salt (1:1) → HCID 49871231, compound

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Reaction Steps

6-[2-(3-Chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione from Step 1 below (1 g, 2.90 mmol) was combined with 5,7-Dimethyl-[1,2,4]triazolo[1,5-α]pyrimidine-2-carbaldehyde (0.5 g, 2.90 mmol) (described in Step 3 of example B(75)) in dry THF (15 mL) with magnetic stirring. To this solution was added AlCl3 (0.76 g, 5.81 mmol) as a soln in THF (6 mL) dropwise over 1 min. The resulting yellow solution was stirred at room temperature for 3 hours. The reaction was quenched with solid Na2CO3.10H2O (1.63 g, 5.81 mmol) and stirred at room temperature for 10 min. Next, the mixture was treated with MgSO4 (2.5 g) and the slurry allowed to stand for 1.5 hours. The yellow mixture was filtered through celite and the filtrate was concentrated. The crude residue was dissolved in EtOAc (50 mL) and treated with PtO2 and stirred with H2 (one balloon pressure). This was maintained for 1 hour then filtered through celite. The filtrate was concentrated and the residue chromatographed on silica gel eluting with CH2Cl2 through 0.75% MeOH in CH2Cl2 to yield the title compound as a white solid. 1H NMR (CDCl3): δ 1.37-1.85 (brm, 8H), 1.98 (m, 2H), 2.37 (m, 1H), 2.49-2.80 (m, 11H), 3.86 (s, 3H), 4.05 (d, J=15.6 Hz, 1H), 4.12 (d, J=15.6 Hz, 1H), 6.81 (d, J=8.6 Hz, 1H), 6.85 (s, 1H), 7.00 (d, J=8.6 Hz, 1H), 7.12 (s, 1H). Anal. Calcd. For C27H31ClN4O4: C, 63.46; H, 6.11; N, 10.96. Found: C, 63.23; H, 6.27; N, 10.74.

Provenance & Evidence