1,1,1-Trimethoxybutane → 4-[(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]tetrahydro-2H-pyran-4-ol

HRID 44754

Reaktionsgleichung

Reaktionsgleichung von HRID 44754
CO[C:3](OC)(OC)[CH2:4][CH2:5][CH3:6].[NH2:11][C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:21]=1[NH:22][CH2:23][C:24]1([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[N:19][CH:18]=[CH:17][CH:16]=2>C1(C)C=CC=CC=1.Cl.N1C=CC=CC=1>[CH2:4]([C:3]1[N:22]([CH2:23][C:24]2([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:21]2[C:20]3[N:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=1)[CH2:5][CH3:6]

Komponenten

5

Edukt 2

HCID 1235121,1,1-TrimethoxybutaneHCID 669191884-[(3-Amino[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol

Produkt 1

HCID 575154594-[(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]tetrahydro-2H-pyran-4-olAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10176127Pyridinium chlorideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Trimethylorthobutyrate (1.9 mL, 12.0 mmol) and pyridine hydrochloride (23 mg, 0.2 mmol) were added to a suspension of 4-[(3-amino[1,5]naphthyridin-4-ylamino)methyl]tetrahydropyran-4-ol (10.0 mmol) in toluene (50 mL). The reaction mixture was heated at reflux overnight and then concentrated under reduced pressure. The residue was triturated with acetonitrile and the resulting solid was isolated by filtration to provide 2.26 g of 4-[(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]tetrahydro-2H-pyran-4-ol as a tan solid.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with acetonitrile
  5. customthe resulting solid was isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-ee4d7896f3c94d31bfbdef497c42ae6c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541438B2

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