Potassium Phosphate, Tribasic → HCID 118037047, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 6-bromo-7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (intermediate 2) (1 g, 3.48 mmol), oxazolidin-2-one (0.364 g, 4.18 mmol), K3PO4 (1.552 g, 7.31 mmol), CuI (0.066 g, 0.348 mmol) and (1S,2S)-cyclohexane-1,2-diamin (0.063 mL, 0.522 mmol) in dioxane (7 ml) was heated to 120° C. for 4 days. Solvents were concentrated and the crude product was purified by silica gel column chromatography eluting with a gradient of MeOH (containing 0.3% of aqueous NH3, 0-10%) in DCM. Product fractions were combined, evaporated and dried to yield the title compound as an orange resin. (UPLC-MS 3) tR 0.44 min; ESI-MS 294.3 [M+H]+. 1H NMR (600 MHz, DMSO-d6) δ 7.14 (s, 1H), 6.83 (s, 1H), 5.12 (s, 1H), 4.39 (dd, 2H), 3.79 (dd, 2H), 3.31-3.19 (m, 8H), 2.69-2.61 (m, 2H), 1.80-1.70 (m, 2H).

Provenance & Evidence