Reserpine → HCID 178486874, compound

Participants

Reaction Steps

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.113 g) and 2-hydroxypyridine N-oxide (0.065 g) were added in turn to a stirred mixture of 2-[4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl]acetic acid (0.1 g), 5-amino-3-methylpyrazole (0.058 g), diisopropylethylamine (0.051 ml) and DMA (1 ml) and the resultant mixture was stirred at ambient temperature for 16 hours. The resultant reaction mixture was transferred onto a Waters ‘β Basic Hypersil’ reversed-phase preparative HPLC column (5 microns silica, 30 mm diameter, 250 mm length) that was eluted with decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. There was thus obtained the title compound (0.064 g); 1H NMR: (DMSOd6) 2.18 (s, 3H), 3.64 (s, 2H), 3.97 (s, 3H), 3.99 (s, 3H), 6.25 (s, 1H), 7.24 (d, 2H), 7.38 (s, 1H), 7.41 (d, 2H), 7.55 (s, 1H), 8.53 (s, 1H), 10.53 (br s, 1H), 11.99 (br s, 1H); Mass Spectrum: M+H+ 420.

Provenance & Evidence