Triethylamine → HCID 66866886, compound

2.54 g (10 mmol) of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (J. Med. Chem. 2001, 44, 1025) and 1.28 g (11 mmol) 2-chloroethylamine hydrochloride were added to 40 ml of anhydrous ethanol. Then 7 ml (50 mmol) of triethylamine were added. The mixture was heated at reflux until the reaction was completed (4 hours). The reaction mixture was concentrated under reduced pressure and 20 ml of saturated aqueous sodium carbonate solution was added. The mixture was extracted with 3×20 ml ethyl acetate. The combined organic layers were washed with 15 ml of water and 15 ml of brine, dried over Na2SO4 and evaporated in vacuo. The crude product (2.88 g) was first purified by flash chromatography on silica gel (petrol ether/ethyl acetate 5:1) and then crystallized from 20 ml of hexane/ethyl acetate=1/1 to afford 1.24 g (42%) of the desired product as a white crystalline solid.

1. temperatureThe mixture was heated
2. temperatureat reflux until the reaction
3. custom(4 hours)
4. concentrationThe reaction mixture was concentrated under reduced pressure and 20 ml of saturated aqueous sodium carbonate solution
5. additionwas added
6. extractionThe mixture was extracted with 3×20 ml ethyl acetate
7. washThe combined organic layers were washed with 15 ml of water and 15 ml of brine
8. dry with materialdried over Na2SO4
9. customevaporated in vacuo
10. customThe crude product (2.88 g) was first purified by flash chromatography on silica gel (petrol ether/ethyl acetate 5:1)
11. customcrystallized from 20 ml of hexane/ethyl acetate=1/1

ORD record

ord-5c624efc5285477c89d916872a6df501

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173609B2