5-(But-2-ynyloxy)pyrazine-2-carboxylic acid → N-(4'-Amino-5'-methylspiro[chroman-4,2'-imidazole]-6-yl)-5-(but-2-ynyloxy)pyrazine-2-carboxamide

Participants

Reaction Steps

The title compound (28 mg, 24% yield) was prepared as described for Example 13a starting from 5-(but-2-ynyloxy)pyrazine-2-carboxylic acid (Intermediate 36, 58 mg, 0.30 mmol) and 5′-methylspiro[chroman-4,2′-imidazole]-4′,6-diamine (Intermediate 30, 63 mg, 0.27 mmol). The crude product was purified by flash chromatography (4 g silica, gradient elution of (EtOAc/MeOH/conc. NH3 (80/20/1) in heptane) followed by preparative chromatography. The pure fractions were combined and evaporated. The residual oil was solidified by evaporation with EtOAc and heptanes: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.85 (t, 3 H), 1.88-1.96 (m, 2 H), 2.23 (s, 3 H), 4.28-4.48 (m, 2 H), 5.07 (q, 2 H), 6.55 (s, 2 H), 6.79 (d, 1 H), 7.02-7.10 (m, 1 H), 7.55-7.64 (m, 1 H), 8.39 (d, 1 H), 8.84 (d, 1 H), 10.26 (s, 1 H); MS (APCI+) m/z 405 [M+H]+.

Provenance & Evidence