Bis(2-Methoxyethyl)amine → N-(3-(trifluoromethyl)benzyl)-2-(5-(bis(2-methoxyethyl)amino)-2-nitrophenyl)isonicotinamide

Temperature

80 °C

Into a 10-mL vial, was placed a solution of bis(2-methoxyethyl)amine (285.6 mg, 2.15 mmol, 3.00 equiv) in N,N-dimethylformamide (3 mL), and N,N-diisopropylethylamine (277 mg, 2.14 mmol, 2.99 equiv). This was followed by the addition of a solution of N-(3-(trifluoromethyl)benzyl)-2-(5-fluoro-2-nitrophenyl)isonicotinamide (300 mg, 0.72 mmol, 1.00 equiv) in N,N-dimethylformamide (2 mL). The resulting solution was stirred for 48 h at 80° C. in an oil bath. The reaction progress was monitored by LCMS. The resulting solution was diluted with 50 mL of water. The resulting solution was extracted with 3×50 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×70 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:5˜1). The product was obtained as 270 mg (71%) of a yellow to green oil.

1. extractionThe resulting solution was extracted with 3×50 mL of ethyl acetate
2. washThe resulting mixture was washed with 2×70 mL of brine
3. dry with materialThe mixture was dried over anhydrous sodium sulfate
4. concentrationconcentrated under vacuum
5. washeluted with ethyl acetate/petroleum ether (1:5˜1)
6. customThe product was obtained as 270 mg (71%) of a yellow to green oil

ORD record

ord-57ec3a57f7c8407c80d4793e829cd407

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09301951B2