Acetic Acid → HCID 131722157, compound

Participants

Reaction Steps

To a solution of pyrimidine-4-carboxylic acid (S)-[7-chloro-3-(3,5-dimethylphenyl)-2-oxo-4-(2-piperidin-2-yl-ethoxy)-1,2-dihydroquinolin-6-yl]-amide (prepared essentially as described in EXAMPLE 2, 9 mg in 0.40 mL methanol) was added 6 mg paraformaldehyde followed by 20 mg powdered 4A molecular sieves and 0.01 mL acetic acid and the mixture stirred at room temperature for 10 minutes. At this time, 5 mg sodium cyanoborohydride was added and the stirring continued. After 2 hours, 0.5 mL tetrahydrofuran was added to ensure homogeneity and after 60 hours the reaction was quenched by the addition of water. The reaction mixture was extracted with methylene chloride and the combined organics washed with brine and dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:10% ammonium hydroxide in methanol, 95:5; then 92:8) gave the title compound (6.7 mg). MASS: 546 (M+H) ##STR167##

Provenance & Evidence