Sodium Hydroxide → HCID 56656504, compound

Participants

Reaction Steps

Acetic acid 2-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-{5-[5-(3-methoxy-azetidin-1-ylmethyl)-pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yl}-benzyl ester (175 mg, 0.26 mmol, Eq: 1.0) was dissolved in 2.6 ml of THF. Sodium hydroxide (1.3 ml of a 1.0M solution in water, 1.3 mmol, Eq: 5.0) was added dropwise. The reaction was stirred at room temperature overnight. Starting material was still present the next morning. The reaction was heated at 50° C. for two hours at which point no starting material remained. The reaction was diluted with ethyl acetate and water and the layers were separated. The organic layer was dried and concentrated. The residue was triturated with isopropyl acetate, filtered, washed with ether, and dried in a vacuum oven to give 75 mg (45.7%) of the desired product as a white powder. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.37 (s, 9H) 2.79 (t, J=6.80 Hz, 2H) 3.11 (s, 3H) 3.37-3.44 (m, 2H) 3.46 (s, 2H) 3.77 (s, 3H) 3.92 (t, J=5.85 Hz, 1H) 4.40 (br.s., 2H) 4.52-4.63 (m, 1H) 7.40-7.62 (m, 5H) 7.74 (d, J=13.22 Hz, 1H) 7.86 (s, 1H) 8.15 (s, 1H) 8.48-8.55 (m, 2H) 9.36-9.44 (m, 1H). MS: (M+H)+=626. MP=140-142° C.

Provenance & Evidence