Triethylamine → 3-(9-((5-chloro-2-((1,5-dimethyl-1H-pyrazol-3-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-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-(1,5-dimethyl-1H-pyrazol-3-yl)-N4-(3-azaspiro[5.5]undecan-9-yl)pyrimidine-2,4-diamine	HCID 118390076	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	3-(9-((5-chloro-2-((1,5-dimethyl-1H-pyrazol-3-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)-3-oxopropanenitrile	HCID 118390112	54.7%

Reaction Steps

To a solution of 5-chloro-N2-(1,5-dimethyl-1H-pyrazol-3-yl)-N4-(3-azaspiro[5.5]undecan-9-yl)pyrimidine-2,4-diamine (200.5 mg, 0.5142 mmol) in dichloromethane (28 mL) and N,N-dimethylformamide (7 mL) were added 2-cyanoacetic acid (110.3 mg, 1.297 mmol), N,N-diethylethanamine (156.5 mg, 1.547 mmol) and HATU (585.4 mg, 1.540 mmol). The mixture was stirred at room temperature for 4 h and concentrated in vacuo. The residue was purified by flash silica gel column chromatography (DCM/MeOH (v/v)=50/1 to 10/1) to give the title compound as a white solid (128.5 mg, 54.68%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09403801B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-5d634bd8640b4284908dbb928bd12948
Source note	uspto-grants-2016_08