4-Methylmorpholine → HCID 11418466, compound

Participants

Reaction Steps

To a 25 mL recovery flask was added [3-(5-methyl-tetrazol-1-yl)-phenoxy]-acetic acid 16 (424 mg, 1.81 mmol, 1.0 eq.) and a stirbar. 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (521 mg, 2.72 mmol, 1.5 eq.) and 1-hydroxybenzotriazole (367 mg, 2.72 mmol, 1.5 eq.) were added to the flask. DMF (12 mL) and N-methylmorpholine (611 μL, 5.44 mmol, 3.0 eq.) were added to the reaction flask. The mixture was allowed to stir for 30 min at room temperature. 5-Amino-2-chlorobenzotrifluoride (709 mg, 3.62 mmol, 2.0 eq.) was added to the flask and the resulting mixture was allowed to stir overnight at room temperature. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with a succession of H2O (1×50 mL), 10% aq. LiCl (3×50 mL), and sat'd aq. NaCl (1×50 mL). The aqueous phases were combined and extracted with ethyl acetate (2×30 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, concentrated and purified by flash chromatography to yield an off-white solid (40 mg, 5%). LC/MSD (HP Series 1100 MSD) MS (ES+) m/z 412.0 (M+H)+1 1H-NMR, Varian 400 MHz (DMSO-d6) δ 10.55 (s, 1H), 8.21 (d, 1H), 7.92-7.89 (m, 1H), 7.70-7.68 (m, 1H), 7.57 (t, 1H), 7.36-7.35 (m, 1H), 7.29-7.27 (m, 2H), 4.85 (s, 2H), 2.53 (s, 3H) ppm.

Provenance & Evidence