Sodium hydride → tert-butyl 4-(5-{[(4-nitro-1-phenyl-1H-pyrazol-3-yl)amino]carbonyl}pyridin-2-yl)piperazine-1-carboxylate

Participants

Reaction Steps

A solution of 4-nitro-1-phenyl-1H-pyrazol-3-amine (0.05 g, 0.25 mmol) in DMF (0.75 mL) was treated with sodium hydride (6 mg (60% in mineral oil), 0.27 mmol). In a separate flask 6-[4-(tert-butoxycarbonyl)piperazin-1-yl]nicotinic acid (0.075 g, 0.25 mmol) in DMF (0.75 mL) was treated with (1H-1,2,3-benzotriazol-1-yloxy)(triisopropyl)phosphonium hexafluorophosphate (0.16 g, 0.37 mmol) and this was stirred at ambient temperature for 1 hour. The acid/BOP solution was then transferred to the nitropyrazole/sodium hydride solution and the resulting reaction mixture was stirred at ambient temperature for 16 hours. The reaction was loaded directly onto a silica cartridge and purified by flash chromatography (20-30% ethyl acetate/hexanes) to give tert-butyl 4-(5-{[(4-nitro-1-phenyl-1H-pyrazol-3-yl)amino]carbonyl}pyridin-2-yl)piperazine-1-carboxylate as a yellow oil. ESIMS calcd 494.2 (M++H), found 494.1 (M++H).

Provenance & Evidence