Hydrochloric Acid → HCID 135410979, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-amino-benzoic acid ethyl ester (0.165 g, 1.0 mmol) in dichloromethane (6 mL ) at about 0° C. was added dropwise with chlorosulfonic acid (0.128 g, 1.1 mmol). The reaction mixture was stirred at 25° C. for 1 h and then phosphorous pentachloride (0.229 g, 1.1 mmol) was added and the reaction mixture heated under reflux for 3.5 hours. The reaction mixture was then cooled to about 25° C. and the solvent evaporated under reduced pressure. A solution of the residue in dichloromethane (10 mL) was treated with the product of Example 205 (0.214 g, 0.5 mmol), followed by triethylamine (0.152 g, 1.5 mmol). The reaction mixture was stirred at 25° C. for 3 hours and then poured into 25 mL of 1N aqueous hydrochloric acid. The reaction mixture was then extracted with dichloromethane (3×25 mL). The combined organics were dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with 0-2% methanol/dichloromethane to provide the title compound (0.166 g, 48% yield). 1H NMR (300 MHz, DMSO-d6) δ 0.98 (d, J=6.25 Hz, 6 H) 1.30 (t, J=7.17 Hz, 3 H) 1.56 (m, 2 H) 1.68 (m, 1 H) 4.29 (q, J=6.99 Hz, 2 H) 4.48 (m, 2 H) 7.44 (m, 4 H) 7.57 (d, J=2.21 Hz, 1 H) 7.62 (dt, J=7.36, 1.47 Hz, 1 H) 7.69 (d, J=8.82 Hz, 1 H) 7.74 (s, 1 H) 8.55 (dd, J=8.09, 1.84 Hz, 1 H) 8.88 (dd, J=4.41, 1.84 Hz, 1 H) 10.80 (s, 1 H) 10.88 (s, 1 H) 14.11 (s, 1 H). MS (ESI+) m/z 655.1 (M+H)+, 672.2 (M+NH4)+, 677.0 (M+Na)+, (ESI−) m/z 653.1 (M−H)−.

Provenance & Evidence