Hydrochloric Acid → 4-[(4-amino-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]piperidin-4-ol dihydrochloride

HRID 44774

Reaktionsgleichung

[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:30][CH3:31])[N:14]([CH2:15][C:16]3([OH:29])[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[C:10]=2[C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[ClH:32]>C(O)C>[ClH:32].[ClH:32].[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:30][CH3:31])[N:14]([CH2:15][C:16]3([OH:29])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:10]=2[C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

Under a nitrogen atmosphere a mixture of tert-butyl 4-[(4-amino-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]-4-hydroxypiperidine-1-carboxylate (6.00 g), aqueous hydrochloric acid (14 mL of 6M), and ethanol (56 mL) was heated at 50° C. overnight. The reaction mixture was concentrated under reduced pressure. The residue was concentrated from methanol 3 times, triturated with acetonitrile, isolated by filtration, washed with acetonitrile, and then dried under high vacuum to provide 5.55 g of 4-[(4-amino-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]piperidin-4-ol dihydrochloride as a tan powder.

Aufarbeitung

concentrationThe reaction mixture was concentrated under reduced pressure
concentrationThe residue was concentrated from methanol 3 times
customtriturated with acetonitrile
customisolated by filtration
washwashed with acetonitrile
customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag: ord-215ce135b4c546299bb936a820830a81
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08541438B2

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