Imidazole → HCID 69943613, compound

Participants

Reaction Conditions

Reaction Steps

Methanesulfonic acid 2-[2-[2-(4-cyano-phenyl)-2-oxo-ethylidene]-5-oxo-4-pyridin-4-ylmethyl-1-((+)-(2,6,6-trimethyl-bicyclo[3.1.1]hept-3-ylmethyl))-imidazolidin-4-yl]-ethyl ester (300 mg, 0.508 mMol) and imidazole (102 mg, 1.5 mMol) were dissolved in anhydrous dimethylformamide (2 mL) under an atmosphere of dry N2. To this mixture was added K2CO3 (207 mg, 1.5 mMol). The mixture was heated to 80° C. for 24 hours after which time it was cooled to ambient temperature and subsequently concentrated under vacuum. The residue was partitioned between CH2Cl2 and water. The CH2Cl2 layer was dried over Na2SO4, filtered and concentrated under vacuum to give a foam. The foam was chromatographed on flash silica gel using a gradient of CHCl3—CH3OH (98:2) to CHCl3—CH3OH (96:4) to give 190 mg of the titled compound as a 1:1 mixture of diastereomers: C.I. m/z 563.4 [M+1]; 1H NMR (CDCl3)δ8.42 (m, 4H), 7.86 (m, 4H), 7.74 (m, 4H), 7.38 (s, 1H), 7.31 (s, 1H), 7.06 (m, 4H), 7.04 (s, 1 H), 7.02 (s, 1H), 6.88 (s, 1H), 6.84 (s, 1H), 5.50 (s, 1H), 5.45 (s, 1H), 3.80-4.10 (m, 4H), 2.90-3.35 (m, 8H), 2.60 (m 2H), 2.26 (m, 4H), 1.20-2.00 (m, 14H), 1.15 (s, 3H), 1.14 (s, 3H), 1.04 (m, 6H), 0.90 (s, 3H), 0.84 (s, 3H).

Provenance & Evidence