Dimethylacetamide → 3-(5-Isopropyl-[1,2,4]triazol-1-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester

Temperature

80 °C

Isobutyramide (6.02 g, 69 mmol) and DMFDMA (9.22 mL) were added to 10 mL of DMA in a first flask, and the mixture was heated to 80° C. with stirring for one hour. In a second flask, a suspension of 3-hydrazino-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester (6.42 g, 23 mmol) was suspended in acetic acid and heated t 80° C. The contents of the first flask were slowly added to the second flask, and the combined mixture was stirred at 80° C. for two hours. The reaction mixture was cooled and concentrated under reduced pressure. The residue was diluted with EtOAc, washed with saturated aqueous NaHCO3 and water, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (hexanes/EtOAc 4:—2:1) to give 2.06 g of 3-(5-isopropyl-[1,2,4]triazol-1-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester as a clear oil, MS (M+H)=337.

1. temperatureheated t 80° C
2. additionThe contents of the first flask were slowly added to the second flask
3. stirringthe combined mixture was stirred at 80° C. for two hours
4. temperatureThe reaction mixture was cooled
5. concentrationconcentrated under reduced pressure
6. additionThe residue was diluted with EtOAc
7. washwashed with saturated aqueous NaHCO3 and water
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified via flash chromatography (hexanes/EtOAc 4:—2:1)

ORD record

ord-8f6e3d13f61645ae870920881c734f7f

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989637B2