Tetrahydrofuran → HCID 25065977, compound

Participants

Reaction Steps

0.25 ml of 2 M dimethylamine/tetrahydrofuran solution and 0.21 mg of sodium triacetoxyborohydride were added to a tetrahydrofuran solution of 166 mg of N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]-3-{[4-(2-oxoethoxy)phenyl]thio}pyridine-2-carboxamide obtained in the step 1, and stirred at room temperature for 30 minutes. Chloroform and saturated saline water were added to it, and extracted with chloroform. The organic layer was dried with anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure, and the residue was purified through reversed-phase middle-pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water/acetonitrile/0.1% trifluoroacetic acid). The solvent of the resulting fraction was evaporated away under reduced pressure to obtain 190 mg of the entitled compound as its trifluoroacetate. The obtained salt was neutralized, extracted with chloroform, and the organic layer was washed with saturated saline water. This was dried with anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure, and the residue was purified through partitioning thin-layer chromatography (NH-PLC05 by Fuji Silicia Chemical, chloroform/methanol=95/5) to obtain 115 mg of the entitled compound as a yellow solid.

Provenance & Evidence