Under a dry atmosphere of nitrogen, 1.0 ml of bromoacetyl bromide (11.4 mmol, 1 equiv) was dissolved in 25 ml of anhydrous dichloromethane, and the mixture was cooled to −40°C. Under vigorous stirring, 1.9 ml of pyridine (22.9 mmol, 2 equiv) in 15 ml of dichloromethane was added slowly and dropwise. The resulting suspension was stirred for a further 30 min and allowed to warm up to −10°C. Successively, 1.9 ml of n-octylamine (11.4 mmol, 1 equiv) in 15 ml of dichloromethane was added dropwise. The yellow reaction mixture was stirred for 60 min between −10°C and room temperature. Termination of the reaction was carried out by addition of water. The biphasic mixture was diluted further with dichloromethane and washed twice with each 1 M hydrochloric acid (aqueous), sodium bicarbonate (saturated, aqueous), and brine. The organic layer was dried over sodium sulfate and filtrated, and the solvent was evaporated under reduced pressure. The resulting orange oil (2.1 g, 8.31 mmol, 73%) was dried in vacuum, and the obtained 2-bromo-N-octylacetamide was used as such in the next reaction step. In 10 ml of N,N-dimethylformamide, 0.45 g of nicotinic acid (3.7 mmol, 1 equiv) and 0.92 g of 2-bromo-N-octylacetamide (3.7 mmol, 1 equiv) were reacted with one another at 70°C for 24 hours. Successively, the solvent was removed under high vacuum, and the obtained residue was purified by automated normal phase column chromatography using a methanol gradient against dichloromethane (0 to 10% from 0 to 20 min, isocratic from 20 to 30 min). The yellowish solid was crystallized from acetone/methanol, and BZ194 was obtained as white crystals (0.67 g, 1.8 mmol, 49%).

Note: The content above has been extracted from a research article, so it may not display correctly.

Please log in to submit your questions online.
Your question will be posted on the Bio-101 website. We will send your questions to the authors of this protocol and Bio-protocol community members who are experienced with this method. you will be informed using the email address associated with your Bio-protocol account.

We use cookies on this site to enhance your user experience. By using our website, you are agreeing to allow the storage of cookies on your computer.