Hydrochloric Acid → HCID 12093794, compound

Participants

Reaction Steps

A Parr bomb was charged with 9 (100 mg, 0.19 mmol), MeOH (10 mL), 1 N HCl (0.2 mL), and catalytic amount of 10% Pd/C. The reaction mixture was exposed to H2 at 38 psi. After 12 h, the reaction was filtered through a pad of Celite® and concentrated in vacuo. The residue was dissolved in CH2Cl2 (10 mL), washed with NaOH (5.0 mL, 30% aqueous), dried (Na2SO4), filtered, and concentrated in vacuo. Chromatography of the residue on silica (8% MeOH/CH2Cl2) provided free base 10 (35 mg, 35%) as a pale yellow solid: ESI-MS m/z: [C28H27N5O4S+H]+ 530; 1H NMR (300 MHz, DMSO-d6) δ 8.42 (s, 1H), 8.12 (d, J=7.5 Hz, 1H), 7.82-7.35 (m, 10H), 4.06 (br t, 2H), 3.80 (s, 2H), 2.79 (s, 3H), 1.83-1.75 (m, 2H), 0.97 (t, J=7.4 Hz, 3H).

Provenance & Evidence