Trifluoroacetic acid → N-(4-(7-((1-(3-methoxypropanoyl)azetidin-3-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3-Methoxypropionic acid	HCID 134442	—
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-(4-(7-(azetidin-3-ylethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide	HCID 71506445	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Acetonitrile	HCID 6342	—
Product	N-(4-(7-((1-(3-methoxypropanoyl)azetidin-3-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide	HCID 71506635	—

Reaction Steps

To a mixture of N-(4-(7-(azetidin-3-ylethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide.trifluoroacetic acid salt (80 mgs, 0.16 mmol), 3-methoxypropanoic acid (0.03 mL, 0.24 mmol), HATU (91 mgs, 0.24 mmol), in N,N-dimethylformamide (1 mL) was added diisopropylethylamine (0.1 mL, 0.41 mmol) and the mixture stirred at room temperature for 16 hours. The reaction mixture was diluted with water and acetonitrile, and the resulting solid was filtered and washed with acetonitrile and ether and dried to give N-(4-(7-((1-(3-methoxypropanoyl)azetidin-3-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide:

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08673966B2
Source dataset	uspto-grants-2014_03
ORD ID	ord-07d2caec63244dd19f17617e2155e0f3
Source note	uspto-grants-2014_03