penta-1,4-dien-3-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of diethyl 2-(3-hydroxy-3-(p-biphenylyl)-propylamino)nonanedioate (5 g), which was prepared via diethyl 2-(3-oxo-3-(p-biphenylyl)propylamino)nonanedioate from the appropriate vinyl ketone using the procedure of Example 2, in absolute ethanol (20 ml) was heated at 60° while nitrourea (1.12 g) was added portion-by-portion. was added portion-by-portion

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Example 11 is repeated by reacting hex-1-en-3-one (preparable starting from butanoyl chloride analogously to the vinyl ketone in Example 11) and 1-piperidino-2-(4'-pentylbiphenyl-4-yl)ethene (preparable analogously to the preparation of the enamine in Example 11) to give 5-(4'-pentylbiphenyl-4-yl)-2-propylpyridine having SE 178° SB 211° SA 222° I.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. concentrate the mixture Purify the residue via column chromatography eluting with 1-10% CH2Cl2/MeOH

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of diethyl 2-(3-hydroxy-3-(p-biphenylyl)-propylamino)nonanedioate (5 g), which was prepared via diethyl 2-(3-oxo-3-(p-biphenylyl)propylamino)nonanedioate from the appropriate vinyl ketone using the procedure of Example 2, in absolute ethanol (20 ml) was heated at 60° while nitrourea (1.12 g) was added portion-by-portion. was added portion-by-portion