Triethylamine → HCID 71269147, compound

Participants

Reaction Steps

To a solution of 301 (crude 1.58 mmol), Et3N (0.33 mL, 2.4 mmol) and DMAP (39 mg, 0.32 mmol) in DCM (25 mL), quinoline-8-sulfonyl chloride (538 mg, 2.37 mmol) in DCM (5 mL) was added dropwise at 0° C. After addition was complete, the solution was left to stir at rt overnight. The mixture was washed with water (2×30 mL) and brine. The organic layer was combined, dried over Na2SO4, concentrated in vacuo. MeOH (10 mL) was added to the residue and the precipitation was filtered to give the desired product (60 mg, 81% over three steps). 1H NMR (500 MHz, CDCl3) δ: 9.07 (m, 1H), 8.51 (d, 1H), 8.13 (d, 1H), 7.93 (d, 1H), 7.57 (t, 1H), 7.44 (m, 1H), 7.29 (d, 1H), 7.12 (m, 2H), 6.98 (m, 1H), 6.90 (m, 3H), 6.59 (d, 2H), 5.76 (d, 1H), 5.53 (d, 1H), 4.34 (m, 1H), 3.61 (m, 1H), 2.59 (m, 1H), 2.27 (t, 1H), 2.07 (m, 1H), 1.88 (m, 1H), 1.60 (m, 1H), 1.34 (m, 1H), 1.24 (m, 1H). MS (ESI+) m/z: 443 [M+H]+.

Provenance & Evidence