10H-Phenothiazine, 10-[(3,4-dihydro-6,7-dimethoxy-1-methyl-2(1H)-isoquinolinyl)carbonyl]- synthesis

Yield:904318-41-8 72%

Reaction Conditions:

with triethylamine in dichloromethane at 20; for 14 h;

Steps:

74

To a stirred solution of 6,7-dimethoxy-l-methyl-l,2,3,4-tetrahydroisoquinoline hydrochloride (70mg, 0.29mmol) in dichloromethane (5mL) was added EPO phenothiazine-10-carbonyl chloride (75mg , 0.29mmol) and Et₃N (60μl, 0.43mmol) and the reaction stirred at r.t. for 14 hours. The reaction mixture was filtered, concentrated in vacuo and purified via flash chromatography eluting with EtOAc/isohexane (1 :4) to afford the title compound as a white crystalline solid. Yield 90mg (72%) : HPLC retention time, 4.32min (Solvent: CH₃CN/H₂O/0.05% NH₃, 5-95% gradient H₂O-6min. Column: Xterra 50 x 4.60 i.d., Cl 8 reverse phase. Flow rate: 1.5mL/min.). Mass spectrum (ES+) m/z 477 (M + H).

References:

WO2006/82354,2006,A1 Location in patent:Page/Page column 37; 38