4-Methylmorpholine → HCID 59560116, compound

Participants

Reaction Steps

To a mixture of 4-(3,5-difluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (113b) (0.308 g, 0.00096 mol), EDCI (0.28 g, 0.0015 mol), HOBt (0.21 g, 0.0015 mol) and NMM (0.49 g, 0.0048 mol) in CH2Cl2 (15 mL) was added 1-methyl-1H-pyrazol-3-amine (0.11 g, 0.001 mol) in one portion. The mixture was stirred at room temperature overnight. The reaction mixture was washed with water, aq. citric acid and then sat. NaHCO3. The organic phase was dried over Na2SO4 and concentrated to give a brown oil. The crude oil was purified by prep. HPLC to give the title compound (95 mg, 51% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.82 (s, 1 H), 7.20 (m, 2 H), 7.03 (d, 2 H), 6.73 (s, 1 H), 6.42 (m, 3 H), 3.72 (s, 3 H), 2.84 (s, 2 H), 1.42 (s, 6 H); LCMS for C21H19F2N3O3 m/z 400.4 (M+H)+.

Provenance & Evidence