Triethylamine → HCID 118390042, compound

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	HCID 118390106	HCID 118390106	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 118390042	HCID 118390042	71.5%

Reaction Steps

To a solution of 5-methyl-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(2-azaspiro[4.4]nonan-4-yl)pyrimidine-2,4-diamine (130 mg, 0.39 mmol) and 2-cyanoacetic acid (36 mg, 0.42 mmol) in a mixture of DCM (5 mL) and DMF (2 mL) were added Et3N (80 mg, 0.79 mmol) and HATU (0.3 g, 0.79 mmol) and the reaction mixture was stirred at rt for 1 h, then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1) to give the product as a yellow solid (0.11 g, 70%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09403801B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-099cd1ebc69c4767814153e12ff99632
Source note	uspto-grants-2016_08