Water → 1-[4-amino-2-ethyl-7-(quinolin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol

HRID 598030

Reaktionsgleichung

Reaktionsgleichung von HRID 598030
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH3:21])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[N:8]=[CH:7][C:6](Br)=[CH:5][C:4]=2[N:3]=1.[N:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25](B(O)O)[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH3:21])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[N:8]=[CH:7][C:6]([C:25]3[CH:24]=[N:23][C:32]4[C:27]([CH:26]=3)=[CH:28][CH:29]=[CH:30][CH:31]=4)=[CH:5][C:4]=2[N:3]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734663Quinoline-3-boronic acidHCID 589706911-(4-amino-7-bromo-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol

Produkt 1

HCID 589707151-[4-amino-2-ethyl-7-(quinolin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-olAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11776TriphenylphosphineKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 10311-PropanolLösungsmittel

Versuchsvorschrift

The method described in Example 152 was used to treat 1-(4-amino-7-bromo-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol (1.0 g, 2.7 mmol) and 3-quinolineboronic acid (0.52 g, 3.0 mmol) in 1-propanol (10 mL) with triphenylphosphine (21.6 mg, 0.0820 mmol), aqueous sodium carbonate (4.1 mL of 2 M), water (2 mL), and palladium (II) acetate (6.2 mg, 0.027 mmol) with the following modifications. The reaction mixture was heated at reflux for four hours. The crude product was purified by recrystallization from ethyl acetate to provide 0.58 g of 1-[4-amino-2-ethyl-7-(quinolin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol as beige needles, mp >270° C.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for four hours
  3. customThe crude product was purified by recrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-02c4350769a44979b83638dbe14990fa
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897609B2

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