N,N-Dimethylethylenediamine → HCID 71468142, compound

Participants

Reaction Steps

4-((2S,4R)-1-Acetyl-2-methyl-4-(phenylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid (for a preparation see Intermediate 35) (90 mg, 0.225 mmol) was dissolved in anhydrous DMF (3 ml and HATU (103 mg, 0.270 mmol) added. DIPEA (0.118 ml, 0.674 mmol) was added to the mixture and after a further 5 min of stirring at r.t. N1,N1-dimethylethane-1,2-diamine (0.030 ml, 0.449 mmol). The reaction mixture was stirred at r.t. overnight, concentrated and partitioned between EtOAc and water. The Organic phase was separated, dried (Na2SO4) and concentrated. The yellow residue was purified by chromatography a silica cartridge (10 g), eluting with MeOH/DCM (1-6% over 120 mls, followed by 6-20% over 120 mls) to give 4-((2S,4R)-1-acetyl-2-methyl-4-(phenylamino)-1,2,3,4-tetrahydroquinolin-6-yl)-N-(2(dimethylamino)ethyl)benzamide (24 mg, 0.05 mmol, 20% yield) as a light brown solid. LCMS (Formic, 2 min), Rt=0.79 min, MH+=471.

Provenance & Evidence