Hydrochloric Acid → HCID 18536740, compound

Participants

Reaction Steps

To a solution of the compound of Example 20 (25.6 mg, 67.7 μmol) in ethanol (2 ml) were added hydroxylamine hydrochloride (9.38 mg, 135 μmol) and successively sodium acetate (11.1 mg, 135 μmol), and the mixture was refluxed for 3 hours. After cooling, the insolubles were filtered off and solvent was distilled off. The residue obtained was dissolved into ethanol (6 ml) and then 10% palladium-carbon (3.00 mg) and successively concentrated hydrochloric acid (0.2 ml) were added, which was stirred for 2 hours at room temperature under hydrogen atmosphere (4 atm, 392 KPa). Catalyst was filtered off using celite and solvent was distilled off. After the residue obtained was dissolved into N,N-dimethylformaldehyde (2 ml), ethyl 4-isocyanatobenzoate (15.5 mg, 81.2 μmol) and successively triethylamine (14.2 μl, 102 μmol) were added and the mixture was stirred for 1 hour at 60° C. Water was added to the residue obtained by distilling off solvent, which was extracted with ethyl acetate. After dried the extract over anhydrous sodium sulfate, solvent was distilled off. A small quantity of ethyl acetate was added to the residue obtained. The crystals were collected by filtration, washed with ethyl acetate, and then air-dried, thereby obtaining 23.2 mg of title compound as greenish yellow powder. Yield 60%.

Provenance & Evidence