Sodium Hydroxide → HCID 178524766, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl 2-((trans-3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)cyclobutyl)amino)thiazole-5-carboxylate, (EXAMPLE 148), (0.35 g, 0.906 mmol) in ethanol (5 mL) was added sodium hydroxide 1.0 N solution (2.72 mL, 2.72 mmol). The reaction mixture was heated to 80° C. for 1 h and concentrated. The residue was diluted with water and the pH of the resulting solution adjusted to 6 by the addition of 1N HCl (3.1 mL) solution. The precipitate formed was filtered and dried under high vacuum to give the title compound 2-((trans-3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)cyclobutyl)amino)thiazole-5-carboxylic acid (0.300 g, 0.806 mmol, 89% yield). m/z: 373.0 (M+1); 1H NMR (400 MHz, DMSO-d6) δ: ppm 12.50 (br. s., 1 H), 8.18-8.51 (m, 1 H), 7.79-8.15 (m, 2 H), 7.35-7.66 (m, 1 H), 5.14 (quin, J=8.26 Hz, 1 H), 4.38 (br. s., 1 H), 3.16-3.31 (m, 2 H), 2.97 (tt, J=7.02, 3.64 Hz, 1 H), 2.31-2.47 (m, 2 H), 0.94-1.13 (m, 4 H).

Provenance & Evidence