Boron tribromide → HCID 86656651, compound

Participants

Reaction Steps

To a solution of ((S)-1-{[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-butyl)-[3-(4-methoxy-phenyl)-propyl]-dimethyl-ammonium trifluoroacetate (Example 120) (313 mg, 0.556 mmol) in DCM (100 mL) is added BBr3 (3.34 mL of a 1M solution in heptane, 3.34 mmol). The reaction mixture is stirred at RT overnight. The reaction mixture is quenched cautiously by the addition of water then the organic solvents are removed in vacuo. Purification by reverse phase column chromatography (Isolute™ C18, 0-50% acetonitrile in water with 0.1% TFA) affords the title compound. M+ 435. 1H NMR (400 MHz, DMSO-d6) δ 8.40 (1H, t), 7.13 (2H, br), 6.89 (2H, d), 6.64 (2H, d), 5.29 (3H, br), 3.79-3.68 (1H, m), 3.57-3.43 (3H, m), 3.37-3.25 (1H, m), 3.04 (3H, s), 3.01 (3H, s), 2.41-2.30 (2H, m), 1.95-1.73 (3H, m), 1.64-1.35 (3H, m), 0.92 (3H, t).

Provenance & Evidence