1-Methylpyrrolidine → HCID 71736063, compound

Participants

Reaction Conditions

Reaction Steps

Add 1-methylpyrrolidine (0.355 mL, 3.34 mmol) to a suspension of prop-1-en-2-yl(3-(3-(3-(3,3-dimethylbutyl)ureido)-4-fluorophenyl)-2-methyl-1,6-naphthyridin-7-yl)carbamate (0.2 g, 0.417 mmol) and dimethylamine hydrochloride (0.136 g, 1.668 mmol) in dioxane (4 mL) and heat at 60° C. overnight. Cool to RT, add satd. NaHCO3, extract with EtOAc (3×), dry the combined organics over MgSO4, concentrate to dryness and purify via silica gel chromatography (EtOAc/Hex) to afford 3-(3-(3-(3-(3,3-dimethylbutyl)ureido)-4-fluorophenyl)-2-methyl-1,6-naphthyridin-7-yl)-1,1-dimethylurea (99 mg, 51%). MS(ESI) m/z: 467.3 (M+H+). Treat the solid with MeCN (2 mL), add 0.1N HCl (2.33 mL, 0.233 mmol), freeze, lyophilize and dry to afford the title compound (76 mg, 71%). 1H NMR (400 MHz, DMSO-d6): δ 9.52 (s, 1H), 9.30 (s, 1H), 8.64 (s, 1H), 8.50 (s, 1H), 8.41 (s, 1H), 8.32 (dd, J=7.9, 2.4 Hz, 1H), 7.35 (dd, J=11.3, 8.4 Hz, 1H), 7.07 (m, 1H), 6.66 (m, 1H), 3.08 (m, 2H), 3.00 (s, 6H), 2.70 (s, 3H), 1.34 (m, 2H), 0.88 (s, 9H); MS(ESI) m/z: 467.3 (M+H+).

Provenance & Evidence