Hydrochloric Acid → 1-(4-(4-Amino-1h-pyrrolo[3,2-c]pyridin-3-yl)phenyl)-3-(2-(4-fluorophenyl)acetyl)urea, hydrochloride salt

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Reaction Steps

2-(4-Fluorophenyl)acetyl isocyanate (Compound C of Example 3, 0.29 M, 0.062 mL, 0.018 mmol, 2.0 eq) was added to a solution of 3-(4-aminophenyl)-1H-pyrrolo[3,2-c]pyridin-4-amine (0.002 g, 0.009 mmol, 1.0 eq) in 1/1 DCM/CH3CN (1 mL) and the reaction mixture was stirred at room temperature for 6 h. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (SiO2, eluting 0-5% MeOH in CHCl3). The appropriate fractions were isolated and concentrated in vacuo. The residue was dissolved in THF (1 mL), cooled to 0° C. and treated with anhydrous 4 N HCl in dioxane (1 mL, 4.0 mmol, 168 eq). The reaction mixture was stirred at 0° C. for 1 h and the resulting heterogeneous solution was concentrated in vacuo. The residue was triturated with Et2O, discarding the filtrate and the solid dried in vacuo to afford the title compound (0.002 g, 50%) as a pale yellow solid. MS(ESI+) m/z 404 (M+H)+.

Provenance & Evidence