1-Hydroxybenzotriazole → 2-(4-Chloro-phenyl)-3-hydroxy-N-[5-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-3-yl]-propionamide

Temperatur

25 °C

2-(4-Chloro-phenyl)-3-hydroxy-propionic acid (570 mg, 2.84 mmol) (Preparation 244) was added to a solution of (5-Amino-pyridin-3-yl)-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone (200 mg, 0.71 mmol) (Preparation 95) in THF (5 mL). Di-isopropyl ethylamine (0.64 mL, 3.56 mmol), EDCI.HCl (273 mg, 1.42 mmol) and HOBT (193 mg, 1.42 mmol) were added and the mixture was stirred at 25° C. for 48 hours. The reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (2 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layer was washed with water (5 mL), brine (5 mL), dried over sodium sulphate and evaporated in vacuo. The crude material was purified by preparative TLC (dichloromethane:methanol 93:7) to afford the title compound as a yellow solid in 3% yield, 10 mg.

1. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (2 mL)
2. extractionextracted with ethyl acetate (3×15 mL)
3. washThe combined organic layer was washed with water (5 mL), brine (5 mL)
4. dry with materialdried over sodium sulphate
5. customevaporated in vacuo
6. customThe crude material was purified by preparative TLC (dichloromethane:methanol 93:7)

ORD-Eintrag

ord-4d2638fba169438e86166e1822b0dc0d

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08846698B2