Reaction Steps
((N-p-Toluenesulfonyl)imidazol-2-yl)methylmethanesulfonate (1.6 g) was added to a suspension of the compound of Description 3 (2.47 g) and potassium carbonate (800 mg) in dimethylformamide (10 ml) and the resulting mixture was heated at 100° C. for 2 h. The mixture was cooled, diluted with water (100 ml) and extracted with ethyl acetate (3×20 ml). The organic extracts were combined, washed with brine, dried (MgSO4) and concentrated in vacuo. This afforded a colourless oil which was purified by column chromatography on silica using 25-30% ethyl acetate in hexane. This afforded the product as a white crystalline solid which was recrystallised from dichloromethane/petrol: mp 125°-126° C. 1H NMR (360 MHz, DMSO-d6) d 1.4-1.5 (1H, m, NCH2CH2CHH), 1.5-1.67 (1H, m, NCH2CH2CHH), 1.8-2.0 (1H, m, NCH2CHH), 2.06-2.1 (1H, m, NCH2CHH), 2.35 (3H, s, CH3), 2.4 (1H, mc, NCHH), 2.7-2.86 (1H, m, NCHH), 3.50 (1H, d, J=14.0 Hz, CHH-imidazole), 3.56 (1H, brs, CHO), 3.76 (1H, d, J=1.5 Hz, CHPh), 4.08 (1H, d, J=14.0 Hz, CHH-imidazole), 4.09 (1H, d, J=12.0 Hz, OCHH), 4.48 (1H, d, J=12.0 Hz, OCHH), 6.96 (1H, d, J=1.0 Hz, imidazole-H), 7.12 (2H, d, J=8.5 Hz, ArH), 7.2-7.3 (3H, m, ArH), 7.34 (1H, d, J=1.0 Hz, imidazole-H), 7.46-7.58 (2H, m, ArH), 7.60 (2H, s, ArH), 7.71 (1H, ArH), 7.79 (2H, d, J=8.5 Hz, ArH); MS (CI+) m/z 638 (M+ +1). Found: C, 58.48; H, 4.78; N, 6.72; S, 4.81. Calcd. for C31H29F6N3O3S: C, 58.39; H, 4.58; N, 6.59; S, 5.03%.
