Phenylpropiolic Acid → HCID 57749102, compound

Participants

Role	Name	HCID	Charge
Reactant	Phenylpropiolic Acid	HCID 69475	—
Reactant	Diisopropylethylamine	HCID 81531	—
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	N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide	HCID 57749361	—
Solvent	Pyridine	HCID 1049	—
Solvent	Sodium Bicarbonate	HCID 516892	—
Product	HCID 57749102	HCID 57749102	18%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (18.6 mg, 0.060 mmol), 3-phenylprop-2-ynic acid (13.1 mg, 0.090 mmol), HATU (48.7 mg, 0.128 mmol), N,N-diisopropylethylamine (35.1 μL, 0.205 mmol) and pyridine (1.5 mL) was stirred at 80° C. for 13 hr. The reaction mixture was diluted with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by preparative HPLC to give the title compound (4.6 mg, 18%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08304557B2
Source dataset	uspto-grants-2012_11
ORD ID	ord-3533e063e8de4b88a2664afc847151bd
Source note	uspto-grants-2012_11