Acetic Acid → (+/-)-{3-[1-(3-Benzyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propylamino]-propyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

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Reaction Steps

A mixture of 2-(1-amino-propyl)-3-benzyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (180 mg, 0.64 mmol), acetic acid (Example 26, 65 μl, 0.95 mmol), 3-oxo-propyl-carbamic acid 9H-fluoren-9-ylmethyl ester (Org. Lett. 2002, 4, 3001–3003), 1,4-dioxane (5 mL), and 4 Å molecular sieves was stirred at room temperature for 15 min then treated with sodium triacetoxyborohydride (112 mg, 0.53 mmol). After 45 min, the reaction was diluted with methylene chloride (25 mL), filtered, washed with saturated sodium bicarbonate, dried (MgSO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/hexanes to give the desired compound (170 mg, 32%): MS (ESI+) 562.2 (M++H).

Provenance & Evidence