Benzoyl isothiocyanate → tert-butyl 5-chloro-3-[(6-oxo-2-thioxo-1,2,6,7-tetrahydro-3H-purin-3-yl)methyl]-1H-indole-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 3-({[5-(aminocarbonyl)-1H-imidazol-4-yl]amino}methyl)-5-chloro-1H-indole-1-carboxylate (0.30 g, 0.78 mmol, obtained from Example 10(b)) and benzoyl isothiocyanate (0.13 mL, 0.94 mmol) in CH2Cl2 (5 mL) was stirred for 2 h and then evaporated. Ammonia (7 M in MeOH, 3 mL) was added to the residue and the mixture was heated to 80° C. for 2 h and then evaporated. Purification by flash chromatography using MeOH (2%) in CHCl3 gave the title compound (0.15 g, 50%). 1H1NMR (DMSO-d6) δ ppm 13.92 (1H), 12.57 (1H), 8.23 (1H), 8.12 (1H), 7.99 (1H), 7.81 (1H), 7.37 (1H), 5.81 (2H), 1.61 (9H); MS (ESI) m/z 430 (M−1).

Provenance & Evidence