Triethylamine → 9-Chloro-3-methyl-5-{1-[2-(pyridin-3-yloxy)-acetyl]-piperidin-3-yl}-5H-isoxazolo[4,3-c]quinolin-4-one

HRID 2212196

Reaktionsgleichung

Reaktionsgleichung von HRID 2212196
I.[Cl:2][C:3]1[C:4]2[C:5]3[C:6](=[C:20]([CH3:23])[O:21][N:22]=3)[C:7](=[O:19])[N:8]([CH:13]3[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1.N1C=CC=CC=1CC[C:32](O)=[O:33].Cl.CN(C)[CH2:38][CH2:39][CH2:40][N:41]=[C:42]=NCC.[OH:47]N1C2N=CC=CC=2N=N1.C(N([CH2:62][CH3:63])CC)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[Cl:2][C:3]1[C:4]2[C:5]3[C:6](=[C:20]([CH3:23])[O:21][N:22]=3)[C:7](=[O:19])[N:8]([CH:13]3[CH2:18][CH2:17][CH2:16][N:15]([C:62](=[O:47])[CH2:63][O:33][C:32]4[CH:42]=[N:41][CH:40]=[CH:39][CH:38]=4)[CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 181649HOAtHCID 5642923-(Pyridin-2-yl)propanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219637129-Chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

Produkt 1

HCID 219636999-Chloro-3-methyl-5-{1-[2-(pyridin-3-yloxy)-acetyl]-piperidin-3-yl}-5H-isoxazolo[4,3-c]quinolin-4-oneAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Add 9-chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide (50 mg, 0.11 mmol), 2-pyridine propionic acid (100 mg, 0.33 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (26 mg, 0.13 mmol), 1-hydroxy-7-azabenzotriazole (18 mg, 0.13 mmol), 4-dimethylamino-pyridine (1 mg, 0.01 mmol), and dimethylformamide (3 mL) to a dry roundbottom flask. Stir the reaction under nitrogen, and add triethylamine (30 μL, 0.22 mmol) dropwise. Stir the solution under nitrogen at room temperature overnight. Concentrate the solution and dissolve in 20% isopropanol/chloroform, washed with saturated aqueous sodium bicarbonate solution, brine, dry over magnesium sulfate and concentrate. Purify by flash chromatography on silica gel (eluting with 0–2% methanol/chloroform) to give 38.5 mg of the title compound as a white solid, 76% yield. 1H NMR: consistent with structure. MS (ion spray) 451 (M+).

Aufarbeitung

  1. customthe reaction under nitrogen
  2. stirringStir the solution under nitrogen at room temperature overnight
  3. concentrationConcentrate the solution
  4. dissolutiondissolve in 20% isopropanol/chloroform
  5. washwashed with saturated aqueous sodium bicarbonate solution, brine
  6. dry with materialdry over magnesium sulfate
  7. concentrationconcentrate
  8. customPurify by flash chromatography on silica gel (eluting with 0–2% methanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-2acb0064197f4046a27b9fbddc1d0c5a
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101891B2

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