5-Aminoimidazole-4-carboxamide hydrochloride → HCID 86631113, compound

Participants

Reaction Steps

A reaction mixture of 4-amino-5-imidazolecarboxamide hydrochloride (0.20 g, 1.23 mmol), tert-butyl 5-fluoro-3-formyl-1H-indole-1-carboxylate (0.39 g, 1.48 mmol, obtained from Example 6(a)), and NaCNBH3 (0.078 g, 1.23 mmol) in methanol (3 mL) was stirred at r.t. for 1 h. Additional 5-fluoro-3-formyl-indole-1-carbonylic acid tert-butyl ester (0.31 equiv.) was added and after stirring at r.t. for 1 h the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water. The aqueous phase was extracted twice with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated. The crude product was purified by flash column chromatography (heptane/ethyl acetate (1:0 to 0:1) then CH2Cl2), obtaining 0.32 g (70%) of the title compound. MS (ESI) m/z 374 (M+1).

Provenance & Evidence