反应详情

A solution of 4-cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide (52.4 mg, 0.113 mmol, as prepared in Example 15, step (h)) in EtOH (2 mL) was treated with (1S)-(+)-10-camphorsulfonic acid (26.4 mg, 0.113 mmol) at room temperature for 1 h. The solvents were evaporated in vacuo, and the residue was dried under high vacuum overnight. The solid was dissolved in a minimum amount of EtOH (1 mL) with sonication and heating. While warm, the solution was slowly treated with hexanes until first precipitate was seen at the surface of the solution. The mixture was allowed to stir 30 min at room temperature while material continued to precipitate. The solid was filtered and air-dried to afford the title compound (66.2 mg, 84%) as white crystals. 1H-NMR (CD3OD; 400 MHz): δ 9.17 (d, 1H, J=8.4 Hz), 8.10 (s, 1H), 7.95 (d, 1H, J=8.4 Hz), 6.39-6.32 (m, 1H), 3.76-3.64 (m, 1H), 3.38-3.34 (m, 2H), 2.80-2.75 (m, 1H), 2.75-2.65 (m, 1H), 2.54-2.45 (m, 2H), 2.40-2.30 (m, 1H), 2.25-2.18 (m, 2H), 2.10-2.00 (m, 2H), 1.98-1.86 (m, 3H), 1.76-1.66 (m, 4H), 1.65-1.56 (m, 1H), 1.47-1.38 (m, 7H), 1.30 (s, 6H), 1.15 (m, 9H), 0.87 (s, 3H). Mass spectrum (APCI, m/z): Calcd. for C27H35N5O2, 462.3 (M+H), found 462.3.

1. customThe solvents were evaporated in vacuo
2. customthe residue was dried under high vacuum overnight
3. dissolutionThe solid was dissolved in a minimum amount of EtOH (1 mL) with sonication
4. temperatureheating
5. temperatureWhile warm
6. additionthe solution was slowly treated with hexanes until first precipitate
7. customto precipitate
8. filtrationThe solid was filtered
9. customair-dried