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

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Cyanoacetic acid	HCID 9740	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)-N4 (octahydrocyclopenta[c]pyrrol-5-yl)pyrimidine-2,4-diamine	HCID 118389986	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	3-(5-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-oxopropanenitrile	HCID 118390119	72.8%

Reaction Steps

To a solution of 5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(octahydrocyclopenta[c]pyrrol-5-yl)pyrimidine-2,4-diamine (401.6 mg, 1.20 mmol), 2-cyanoacetic acid (110.3 mg, 1.30 mmol) in a mixture of DCM and DMF (4/1 (v/v)), 50 mL) were added HATU (555.6 mg, 1.46 mmol) and Et3N (375.6 mg, 3.71 mmol). The reaction mixture was stirred at rt overnight, 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, concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=50/1) to give the title compound as a beige solid (350 mg, 72.8%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09403801B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-875880650cdd4e0ca2a3d1b5778e9e62
Source note	uspto-grants-2016_08