Triethylamine → 3-(9-((5-chloro-2-((1-methyl-1H-pyrazol-4-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-methyl-1H-pyrazol-4-yl)-N4-(3-azaspiro[5.5]undecan-9-yl) pyrimidine-2,4-diamine	HCID 118390069	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	3-(9-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)-3-oxopropanenitrile	HCID 118389994	85.5%

Reaction Steps

To a solution of 5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(3-azaspiro[5.5]undecan-9-yl)pyrimidine-2,4-diamine (54.0 mg, 0.14 mmol) in a mixture of dichloromethane and DMF (8 mL/2 mL) were added 2-cyanoacetic acid (30.7 mg, 0.36 mmol), Et3N (52.1 mg, 0.52 mmol) and HATU (164.2 mg, 0.43 mmol). The mixture was stirred at room temperature overnight and then concentrated in vacuo. The residue was purified by preparative TLC (MeOH/DCM (V/V)=1/10) to give the title compound as a light yellow solid (53.0 mg, 83.3%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09403801B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-e7af401265fc4a60a8671811dabcac80
Source note	uspto-grants-2016_08