Hydrazine hydrate (1:1) → HCID 178440924, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7-[(2-acetylpyridin-4-yl)oxy]-N-(3-tert-butylphenyl)-1,2,3,4-tetrahydronaphthalene-2-carboxamide (0.516 g, 1.16 mmol) in 1,1-dimethoxy-N,N-dimethylmethanamine (20 mL) was allowed to stir at 115° C. for 12 h. The reaction mixture was concentrated. The residue was dissolved in ethanol (20 mL) and hydrazine hydrate (0.600 mL, 12.3 mmol) was added. The reaction mixture was allowed to stir at 90° C. for 1 h and then diluted with water. The solution was extracted with EtOAc and the combined organic solutions were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give N-(3-tert-butylphenyl)-7-{[2-(1H-pyrazol-3-yl)-pyridin-4-yl]oxy}-1,2,3,4-tetrahydronaphthalene-2-carboxamide 1-231 (0.184 g, 0.394 mmol, 34%) as a white solid. 1H NMR (400 MHz, d6-DMSO, HCl salt) δ: 10.02 (s, 1H), 8.63-8.51 (m, 1H), 8.05-7.96 (m, 1H), 7.85-7.77 (m, 1H), 7.68-7.62 (m, 1H), 7.54-7.46 (m, 1H), 7.37-7.03 (m, 7H), 3.06-2.73 (m, 5H), 2.18-2.05 (m, 1H), 1.88-1.74 (m, 1H), and 1.25 (s, 9H). LCMS: (FA) ES+467.8, ES−465.5.

Provenance & Evidence