Phenol → HCID 24786069, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylene]amino}thiophene-2-carboxylate (0.388 g, 1.20 mmol) and 1-{2-[(1-methylpiperidin-4-yl)oxy]pyridin-4-yl}methanamine (0.242 g, 1.09 mmol, from step b above) were mixed with 1.0 g of phenol and heated to 120° C. for 2 h. The mixture was purified by preparative HPLC (Kromasil C8-50×250 mm, CH3CN/0, 1 M NH4OAc 5/95-50/50 and CH3CN/0, 2% HOAc 5/95-50/50). The product was freeze dried from water. Yield: 0.154 g (27%). 1H NMR (400 MHz, DMSO-d6) δ 8.63 (s, 1H), 8.09 (d, 1H), 7.94 (s, 1H), 7.90 (m, 2H), 7.58 (m, 2H), 6.88 (m, 1H), 6.60 (bs, 1H), 5.20 (s, 2H), 4.95 (m, 1H), 2.60 (m, 2H), 2.15 (s, 3H), 2.12 (m, 2H), 1.92 (m, 2H), 1.62 (m, 2H). 13C NMR (100 MHz, DMSO-d6) δ 163.7, 158.6, 156.8, 150.6, 149.4, 147.9, 135.1, 131.9, 130.0, 128.7, 122.5, 122.4, 116.1, 109.7, 53.4, 48.5, 46.5, 31.3. MS (ESI+) 467/469 (M+1H+).

Provenance & Evidence