Water → HCID 59225636, compound

Participants

Reaction Steps

Methyl 3-(2-(3-(benzyloxy)-5-bromopyrazin-2-ylamino)thiazol-4-yl)propanoate (0.826 g, 1.84 mmol), 9-benzyl-9-bora-bicyclo[3.3.1]nonane (11.0 mL, 5.51 mmol), PdCl2(dppf) dichloromethane adduct (0.151 g, 0.184 mmol), were placed in DMF (25 mL), and water (2.5 mL) and heated to 60° C. for 90 minutes. Cooled reaction mixture to room temperature and partitioned between water and DCM. Layers were separated, dried, filtered, and concentrated. Purified by silica gel to give methyl 3-(2-(5-benzyl-3-(benzyloxy)pyrazin-2-ylamino)thiazol-4-yl)propanoate (0.667 g, 78.8% yield). 28 mg of this was dissolved in DCM and 2M HCl was added and concentrated to give methyl 3-(2-(5-benzyl-3-(benzyloxy)pyrazin-2-ylamino)thiazol-4-yl)propanoate hydrochloride (0.027 g, 93%) 1H NMR (DMSO-d6) δ 7.79 (s, 1H), 7.52 (m, 2H), 7.32 (m, 4H), 7.27 (d, 4H), 7.20 (m, 1H), 5.44 (s, 2H), 3.93 (s, 2H), 3.60 (s, 3H), 2.86 (m, 2H), 2.68 (m, 2H). Mass spectrum (apci) m/z=461.1.0 (M+H-HCl).

Provenance & Evidence