反应详情

Solid (±)-tert-butyl 3-(4-(2-phenylpyrimidin-5-yl)-1H-imidazol-2-yl)piperidine-1-carboxylate (Example 21) was treated with 0.5 mL of trifluoroacetic acid at room temperature for 0.5 hour. Three times the reaction mixture was diluted with toluene and concentrated to give a dark semi-solid. The crude material was chromatographed on silica (4 g) eluted with 1:10:90 v/v acetic acid-methanol-dichloromethane. The clean fractions were collected, concentrated under reduced pressure, and the material was three times diluted with toluene and concentrated, then dried under high vacuum to afford the title compound as a pale yellow solid; Rf 0.17 with 1:10:90 v/v acetic acid-methanol-dichloromethane; melting point 140° C.; 1H-NMR (400 MHz; DMSO-d6) δ 9.22 (s, 2H), 8.5-9.2 (br s, 2H), 8.35-8.45 (m, 2H), 7.9 (d, 1H), 7.4-7.5 (m, 3H), 3.4-3.6 (m, 2H), 3.2-3.4 (m, 2H), 2.9-3.1 (m, 1H), 2.0-2.2 (m, 1H), 1.6-1.9 (m, 3H); MS (ESI+) m/z 306 (M+1); H-PGDS FPBA IC50: 1.25 μM.

1. concentrationconcentrated
2. customto give a dark semi-solid
3. customThe crude material was chromatographed on silica (4 g)
4. washeluted with 1:10:90 v/v acetic acid-methanol-dichloromethane
5. customThe clean fractions were collected
6. concentrationconcentrated under reduced pressure
7. additiondiluted with toluene
8. concentrationconcentrated
9. customdried under high vacuum