5-(BROMOMETHYL)-3-METHYLISOXAZOLE

To a stirred solution of acetaldehyde oxime (10 g, 169.49mmol) in DCM (200 mL) was added propargyl bromide (13 mL, 169.49mmol) followed by triethylamine (10 mL) at 0°C, then 4percent NaOCI (1 .08 mL) was added drop wise to the reaction mixture at 0°C. After that the reaction mixture was stirred at room temperature for 3h. Reaction mixture was extracted with DCM (3x 200 mL) dried over Na2S0General procedure: Amine (0.25 mmol), and bromide (0.25 mmol) were taken up in acetonitrile (0.3 mL) in a conical vial equipped with a stirrer bar. Potassium carbonate (0.5 mmol) was added followed by potassium iodide (10 mol%) if required. The vial was sealed with a screwcap and the reaction was stirred at 40 C until thin layer chromatography (TLC) indicated complete consumption of the starting materials. A precipitate was formed during the reaction which was removed by filtration and the filtrate concentrated under reduced pressure. The residue was purified by flash column chromatography and sent to the Netherlands Cancer Institute (NKI) for biological testing.General procedure: Amine (0.25 mmol), and bromide (0.25 mmol) were taken up in acetonitrile (0.3 mL) in a conical vial equipped with a stirrer bar. Potassium carbonate (0.5 mmol) was added followed by potassium iodide (10 mol%) if required. The vial was sealed with a screwcap and the reaction was stirred at 40 C until thin layer chromatography (TLC) indicated complete consumption of the starting materials. A precipitate was formed during the reaction which was removed by filtration and the filtrate concentrated under reduced pressure. The residue was purified by flash column chromatography and sent to the Netherlands Cancer Institute (NKI) for biological testing.Methyl (5RS)-2-[(3-methyl-1, 2-oxazol-5-yl)methyl]-3-oxo-2, 3, 5, 6, 7, 8-hexahydro[1, 2, 4]triazolo[4, 3-a]pyridine-5-carboxylate (Racemate) Methyl (5RS)-3-oxo-2, 3, 5, 6, 7, 8-hexahydro[1, 2, 4]triazolo[4, 3-a]pyridine-5-carboxylate (racemate) (200 mg, 1.01 mmol) was initially charged in acetonitrile (10 ml). Caesium carbonate (347 mg, 1.06 mmol) and (5RS)-2-[(3-Methyl-1, 2-oxazol-5-yl)methyl]-5-(pyrrolidin-1-ylcarbonyl)-5, 6, 7, 8-tetrahydro[1, 2, 4]triazolo[4, 3-a]pyridin-3(2H)-one (Racemate) (5RS)-5-(Pyrrolidin-1-ylcarbonyl)-5, 6, 7, 8-tetrahydro[1, 2, 4]triazolo[4, 3-a]pyridin-3(2H)-one (racemate) (40.0 mg, 169 mumol) was initially charged in acetonitrile (2.0 ml). Caesium carbonate (82.7 mg, 254 mumol) and

Molecular Weight:176.01
XLogP3:1.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:174.96328
Monoisotopic Mass:174.96328
Topological Polar Surface Area:26
Heavy Atom Count:8
Complexity:78.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes