Isonicotinoyl chloride hydrochloride → Hydrochloric Acid

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Isonicotinoyl chloride hydrochloride	HCID 12262826	—
Edukt	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	—
Lösungsmittel	Tetrahydrofuran	HCID 8028	—
Lösungsmittel	N-methyl-2-pyrrolidone	HCID 13387	—
Produkt	Hydrochloric Acid	HCID 313	—
Produkt	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}-isonicotinamide hydrochloride	HCID 66629861	—

Reaktionsschritte

A mixture comprising 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 (Example 22 step 4) (20 mg, 33 μmol) in THF (0.5 ml) and NMP (0.5 ml) is treated with TEA (13 mg, 0.13 mmol) followed by isonicotinoyl chloride hydrochloride (16 mg, 83 μmol). After stirring at room temperature for 2 hours, the solvent is removed in vacuo and 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+ 708.4)

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08258141B2
Quelldatensatz	uspto-grants-2012_09
ORD ID	ord-adb39d173d3d473fb85e1a6db5973e04
Quellennotiz	uspto-grants-2012_09