Hydrochloric Acid → HCID 67811385, compound

Participants

Reaction Steps

A solution of 1-(3-((((2R,3S,4R,5R)-5-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(isopropyl)amino)propyl)-3-(4-(tert-butyl)phenyl)urea (1.64 g, 3.04 mmol) in 50 mL 50% aq methanol was treated with 1.0N of hydrogen chloride in water (3.87 mL, 3.04 mmol). The solution was concentrated to remove most of the methanol and lyophilized overnight. The cloudy mixture was filtered through a fine frit and the filtrate was concentrated in vacuo to remove the MeOH. The resultant solution was lyophilized overnight to yield the title compound (1.70 g, 97%) as a solid: MS (ESI+) for C28H41N7O4 m/z 540.4 (M+H)+; MS (ESI+) for C28H41N7O4 m/z 538.4 (M+H)+, m/z 574.4 (M+Cl)−; HPLC purity 97% (ret. time, 2.88 min); 1H NMR (400 MHz, d4-MeOH) ppm 8.12 (s, 1H), 7.29 (m, 2H), 7.23 (m, 3H), 6.68 (m, 1H), 6.09 (br. s., 1H), 4.57 (m, 1H), 4.35 (m, 2H), 3.79 (br. s., 1H), 3.55 (m, 2H), 3.26 (br. s., 4H), 1.94 (m, 2H), 1.35 (m, 6H), 1.29 (s, 9H). IC50<10 nM.

Provenance & Evidence