Figure 1.

Small molecule inhibitors of fIXa and fXa. (A) Preparation of tricyclic pyrazolo‐pyridine analogs. Reagents and conditions: (a) lithium di‐isopropylamide, hexamethylphosphoramide, tetrahydrofuran, −78°C; (b) t‐butyl hydrazine hydrochloride, ethanol, room temperature; (c) 37% hydrochloric acid, 125°C, sealed tube, 30 min; (d) 2‐chloro‐4‐(5‐(methoxycarbonyl)‐1H‐benzo[d]imidazol‐1‐yl)benzoic acid, O‐(7‐azabenzotriazole‐1‐yl)‐1,1,3,3‐tetramethyluronium hexafluorophosphate, di‐isopropyl ethyl amine, dimethyl formamide, room temperature then sodium hydroxide. (B) Structure of apixaban.