1,2-Dichloroethane → HCID 178445682, compound

Participants

Reaction Steps

To a solution of the intermediate from step H (65 mg, 0.122 mmol) in DMF (2 mL) was added HOAt (25 mg, 0.184 mmol), β-alanine-tert-butyl ester (34 mg, 0.184 mmol), DIEA (64 μL, 0.37 mmol) and EDC (36 mg, 0.184 mmol). After stirring the reaction at room temperature for 18 hours, the reaction was diluted with ethyl acetate and washed with 1N HCl , saturated NaHCO3 and saturated NaCl solution. The organic layer was dried over anhydrous Na2SO4 filtered and concentrated in vacuo. The residue was purified by flash chromatography using 30% ethyl acetate-hexanes. Colorless oil was obtained. This material was dissolved in DCM (2 mL) and TFA was added (2 mL). After 1 hour the reaction mixture was concentrated in vacuo and azeotroped with toluene (3×) to give the title compound as a solid. 1H NMR (DMSO, 500 MHz): 8.88 (d, J=1.4 Hz, 1H), 8.72 (t, J=5.4 Hz, 1H), 8.2 (d, J=8.7 Hz, 1H), 8.14 (dd, J=2.3, 8.2 Hz, 1H), 8.02 (d, J=1.8 Hz, 1H), 7.81 (dd, J=2.0, 8.5 Hz, 1H), 7.71 (d, J=8.4 Hz, 1H), 7.48 (s, 1H), 7.15 (d, J=8.0 Hz, 1H), 5.85 (s, 2H), 3.48 (q, J=6.9 Hz, 2H), 1.83 (bd, J=12.6 Hz, 2H), 1.45 (m, 4H), 1.25 (m, 2H), 0.98 (m, 1H), 0.83 (s, 9H). LC-MS=3.99 min, (M+H)=600.2.

Provenance & Evidence