反应详情

温度

-30 °C

To a solution of 4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine (220 mg, 0.83 mmol) in dry tetrahydrofurane (10 ml) at −70° C. is slowly added a solution of tert.butyllithium (1.1 ml of a 1.5 M solution in pentane corresponding to 1.65 mmol) and the remaining suspension slowly warmed to about −30° C. At this time, a solution of 2-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-3-methyl-3H-imidazole-4-carboxylic acid phenyl ester (252 mg, 0.83 mmol) in tetrahydrofurane (4 ml) was added and the mixture stirred for 1 h at room temperature. The reaction mixture was treated with saturated aqueous ammonium chloride solution (10 ml) followed by ethyl acetate (20 ml) and the formed precipitate collected. The phases were separated and the aqueous phase extracted three times with ethyl acetate. The combined organic layers were extracted twice with water, dried with magnesium sulfate and evaporated to dryness to yield another batch of raw product. Flash-chromatography on silica (eluent trichloromethane containing 30% of ethyl acetate) yielded the title compound as white solid (31% yield). MS: m/e=475(M+H+), mp 176-178° C.

1. customthe formed precipitate collected
2. customThe phases were separated
3. extractionthe aqueous phase extracted three times with ethyl acetate
4. extractionThe combined organic layers were extracted twice with water
5. dry with materialdried with magnesium sulfate
6. customevaporated to dryness
7. customto yield another batch of raw product