N-methyl-2-pyrrolidone → Hydrochloric Acid

Participants

Role	Name	HCID	Charge
Reactant	N-methyl-2-pyrrolidone	HCID 13387	—
Reactant	6-Morpholinonicotinoyl Chloride	HCID 2776461	—
Reactant	N-((1S,2R,3S,4R)-4-{2-((R)-3-Amino-pyrrolidin-1-yl)-6-[2,2-bis-(4-hydroxy-phenyl)-ethylamino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide	HCID 66630815	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	Hydrochloric Acid	HCID 313	—
Product	N-{(R)-1-[6-[2,2-Bis-(4-hydroxy-phenyl)-ethylamino]-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-2-yl]-pyrrolidin-3-yl}-6-morpholin-4-yl-nicotinamide hydrochloride	HCID 66630618	—

Reaction Steps

A suspension of N-((1S,2R,3S,4R)-4-{2-((R)-3-amino-pyrrolidin-1-yl)-6-[2,2-bis-(4-hydroxy-phenyl)-ethylamino]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide (20 mg, 33 μmol) in dry THF is treated with NMP (0.5 ml) followed by TEA (13.4 mg, 0.13 mmol) and 6-morpholinonicotinoyl chloride (8.3 mg, 37 μmol). The reaction mixture is stirred at room temperature for 30 minutes and then the solvent is removed in vacuo. Purification by C-18 reverse phase column chromatography eluting with acetonitrile:water:HCl (0.1%) (gradient of 0 to 100% acetonitrile) yields the title compound. (MH+ 793.4)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08258141B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-03735d279b284683a28097a584156cbe
Source note	uspto-grants-2012_09