(2-Methoxyethyl)(methyl)amine → 4-[4-methoxy-2-(4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-benzoylamino)-benzothiazol-7-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.30 g (0.58 mMol) 4-[2-(4-chloromethyl-benzoylamino)-4-methoxy-benzothiazol-7-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester in 10 ml THF were added 0.16 g (1.75 mMol) N-(2-methoxyethyl)-methyl amine. The reaction mixture was heated to 70° C. for 5 h. The solvent was evaporated to dryness, the residue taken up in ethyl acetate and washed with water and brine. The organic phase was dried over sodium sulfate and evaporated to dryness in vacuo. The residue was subjected to column chromatography (dichloro methane/methanol 19:1) to yield 0.27 g (82%) of 4-[4-methoxy-2-(4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-benzoylamino)-benzothiazol-7-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as a white foam. ES-MS m/e (%): 567 ([M+H]+, 100).

Provenance & Evidence