4-Methylmorpholine → N-[1-(3,3-dimethoxypropyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide

Participants

Reaction Steps

A mixture of 1-(3,3-dimethoxypropyl)-1H-indazole-6-ylamine (1.32 g, 5.60 mmol), 4-phenoxyphenylacetic acid (1.34 g, 5.88 mmol), N-methyl morpholine (1.47 mL, 13.4 mmol), HOBt (945 mg, 7.0 mmol), and ethyldimethylpropylcarbodiimide hydrochloride (1.34 g, 7.0 mmol) in DMF (28 mL) was stirred at room temperature for 3 hours followed by the addition of H2O (40 mL) and diethyl ether (30 mL). The layers were separated, and the aqueous was extracted with diethyl ether (3×30 mL). The combined organic layers were dried (Na2SO4), filtered, concentrated under reduced pressure and purified by MPLC (SiO2, 1:1 hexane:ethyl acetate to 1:3 hexane:ethyl acetate) to provide the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 2.05 (m, 2 H), 3.22 (m, 6 H), 3.68 (s, 2 H), 4.29 (m, 3 H), 6.99 (m, 4 H), 7.14 (m, 2 H), 7.38 (m, 4 H), 7.66 (m, 1 H), 7.97 (s, 1 H), 8.12 (s, 1 H), and 10.34 (s, 1 H); MS (ESI) 444 (M−H)−.

Provenance & Evidence