Chloride → HCID 178482329, compound

Participants

Reaction Steps

To a solution of 6,7-dimethoxy-1-methyl-4-((6-(methylamino)-[1,3]dioxolo[4,5-g]quinolin-7-yl)methyl)isoquinolin-3-ol 60 free base (28 mg, 65 μmol) in dry CH2Cl2 (5 mL) at 0° C. in a 25 mL round-bottomed flask equipped with a magnetic stirrer under N2 was added dropwise BCl3 (1.0 N solution in CH2Cl2, 0.30 mL, 0.30 mmol). After complete addition, the bath was immediately removed and stirring was continued overnight at RT. The reaction mixture was then carefully quenched with MeOH (3 mL) and the mixture was concentrated to dryness at 40° C. under vacuum before purification by prep. HPLC (eluent H2O:CH3CN:TFA=100:0:0.05 to 60:40:0.05 in 10 min) and lyophilisation. The residue was then dissolved in a 0.19 N HCl solution in MeOH (5 mL) before concentration at 40° C. under vacuum. Ion exchange on Amberlite IRA-400 (chloride form, 50 eq.) finally afforded 3-((3-hydroxy-6,7-dimethoxy-1-methylisoquinolin-4-yl)methyl)-2-(methylamino)quinoline-6,7-diol dihydrochloride 59 as a brown solid (10 mg, 31% yield).

Provenance & Evidence