Dimethylformamide → HCID 89690426, compound

In a 250 ml round bottom flask equipped with a magnetic stir bar, the potassium carbonate (2.06 g, 14.91 mmol) was suspended in clean, dry N,N-dimethylformamide (50.00 ml, 645.74 mmol) and the mixture was stirred together under nitrogen at room temperature as the 2-chloro-5-nitro-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid 1d (2.54 g, 6.76 mmol) was added in one portion. The mixture was stirred until it appeared all the organic solids were in solution and then iodomethane (0.46 ml, 7.39 mmol) was added. The reaction was diluted with 100 ml of water and the product was extracted from the aqueous using ethyl acetate (3×100 ml). The layers were separated and the organic phases were combined, washed with brine (1×150 ml) and saturated aqueous lithium chloride solution (2×150 ml). The solution was then dried over Na2SO4; the solution was decanted and the solvent was removed under reduced pressure. The compound was purified using silica gel column chromatography, eluting a gradient of 100% heptanes to 75% ethyl acetate in heptane. 2-Chloro-5-nitro-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid methyl ester 10a (2.45 g, 6.27 mmol) was isolated as a yellowish-white solid and was carried on without further purification. LCMS (m/e)=390 (M+H).

1. customIn a 250 ml round bottom flask equipped with a magnetic stir bar
2. additionwas added in one portion
3. extractionthe product was extracted from the
4. customThe layers were separated
5. washwashed with brine (1×150 ml) and saturated aqueous lithium chloride solution (2×150 ml)
6. dry with materialThe solution was then dried over Na2SO4
7. customthe solution was decanted
8. customthe solvent was removed under reduced pressure
9. customThe compound was purified
10. washeluting a gradient of 100% heptanes to 75% ethyl acetate in heptane

ORD record

ord-95e118dec870468eaa07a70d7e9cd5cc

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409897B2