Triethylamine → 7-{4-[4-(2,3-Dichloro-phenyl)-piperazin-1-yl]-butoxy}-4-methyl-3,4-dihydro-1H-[1,8]naphthyridin-2-one

HRID 1373587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373587
[CH3:1][CH:2]1[CH2:11][C:10](=[O:12])[NH:9][C:8]2[N:7]=[C:6]([O:13][CH2:14][CH2:15][CH2:16][CH:17]=O)[CH:5]=[CH:4][C:3]1=2.Cl.[Cl:20][C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:20][C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[N:28]1[CH2:33][CH2:32][N:31]([CH2:17][CH2:16][CH2:15][CH2:14][O:13][C:6]2[N:7]=[C:8]3[C:3]([CH:2]([CH3:1])[CH2:11][C:10](=[O:12])[NH:9]3)=[CH:4][CH:5]=2)[CH2:30][CH2:29]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochlorideHCID 21073357HCID 21073357, Verbindung

Produkt 1

HCID 210735467-{4-[4-(2,3-Dichloro-phenyl)-piperazin-1-yl]-butoxy}-4-methyl-3,4-dihydro-1H-[1,8]naphthyridin-2-oneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

The crude 4-(5-methyl-7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde in 1,2-dichloroethane (50 mL) is treated with 1-(2,3-dichlorophenyl)piperazine monohydrochloride (1.104 g, 4.13 mmol), followed by triethylamine (0.80 mL, 5.69 mmol) and sodium triacetoxyborohydride (0.911 g, 4.30 mmol). The cloudy yellow solution is stirred at room temperature for 1 hour. The mixture is quenched with water and saturated NaHCO3 solution and extracted with CH2Cl2. The organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to a yellow oil. The oil is purified by column chromatography (5:95 methanol/ethyl acetate) to afford the title compound (1.08 g, 79% over 2 steps) as a white solid. Mp 53–54° C. 1H NMR (CDCl3, 400 MHz): δ 8.94 (br s, 1H), 7.83 (d, 1H), 7.18–7.13 (m, 2H), 6.98–6.94 (m, 1H), 6.62 (d, 1H), 6.38 (d, 1H), 4.38 (t, 2H), 3.16–3.02 (m, 4H), 2.76–2.60 (m, 4H), 2.55–2.46 (m, 2H), 1.90–1.82 (m, 2H), 1.77–1.64 (m, 2H). MS ES: m/z=462.72, 464.58.

Aufarbeitung

  1. customThe mixture is quenched with water and saturated NaHCO3 solution
  2. extractionextracted with CH2Cl2
  3. washThe organic extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum to a yellow oil
  7. customThe oil is purified by column chromatography (5:95 methanol/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-b58efd3bb1754f3e942d0fcece2eaffe
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07160888B2

Notizen zur Reaktion

Wird geladen…