Triethylamine → 3-(5-((5-chloro-2-((1,5-dimethyl-1H-pyrazol-3-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-oxopropanenitrile

To a solution of 5-chloro-N2-(1,5-dimethyl-1H-pyrazol-3-yl)-N4-(octahydro cyclopenta[c]pyrrol-5-yl)pyrimidine-2,4-diamine (522.0 mg, 1.50 mmol) and 2-cyanoacetic acid (127.6 mg, 1.50 mmol) in a mixture of DCM (40 mL) and DMF (10 mL) were added HATU (690.2 mg, 1.82 mmol) and Et3N (313.5 mg, 3.10 mmol). After addition, the reaction mixture was stirred at rt for 1.5 h, then quenched with H2O (30 mL) and extracted with DCM (100 mL×3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=80/1) to give the title compound as a beige solid (455.2 mg, 73.1%).

1. additionAfter addition
2. customquenched with H2O (30 mL)
3. extractionextracted with DCM (100 mL×3)
4. washThe combined organic phases were washed with brine (100 mL)
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=80/1)

ORD record

ord-21cfe918d50c4e66a9fb042b7051bc16

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403801B2