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	US08318750B2
Quelldatensatz	uspto-grants-2012_11
ORD ID	ord-1a44f918f635453098f935faaafa6e0a
Quellennotiz	uspto-grants-2012_11