Benzo(d)thiazol-2-amine → N-Benzothiazol-2-yl-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide

Participants

Reaction Steps

This compound was prepared via BOP coupling of (S)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (prepared in Example 1, Step A, 144 mg; 0.5 mmol) and 2-amino-benzothiazole (81 mg; 0.55 mmol) in a manner similar to that used for the preparation of (S)-3-cyclohexyl-2-( 1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide (outlined in Example 9, Step B) to provide crude N-Benzothiazol-2-yl-3-cyclohexyl-2-( 1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide. The crude product was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, eluent: 35% ethyl acetate/hexanes) to give 185 mg (44%) of N-Benzothiazol-2-yl-3-cyclohexyl-2-( 1-oxo-1,3-dihydro-isoindol-2-yl)-propionamide as a white solid: EI-HRMS m/e calcd for C24H25N3O2S (M+) 419.1667, found 419.1661.

Provenance & Evidence