1,4-Pentadien-3-one → 3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-N-[(S)-6-(4-oxo-piperidin-1-yl)-4,5,6,7-tetrahydro-benzothiazol-2-yl]-benzamide

Participants

Reaction Steps

Add a solution of divinyl ketone (0.08 g 1.03 mmol) in 1 mL of CH2Cl2 to a solution of N—((S)-6-amino-4,5,6,7-tetrahydro-benzothiazol-2-yl)-3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzamide (0.47 g, 1.03 mmol) in 10 mL of CH2Cl2 and 10 mL of MeOH. Stir the solution for 3 h at room temperature and concentrate the mixture. Purify the residue via column chromatography eluting with 1-10% CH2Cl2/MeOH to give 0.16 g, 30% yield of 3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-N—[(S)-6-(4-oxo-piperidin-1-yl)-4,5,6,7-tetrahydro-benzothiazol-2-yl]-benzamide. Both 1 cms and NMR show that the product exists as a mixture of ketone and hydrate. MS, ES+ 555.70 (M+H2O+H), rt 1.21 min.

Provenance & Evidence