Potassium Iodide → 2-[3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidin-1-yl]-N-(3,4,5-trimethoxy-phenyl)-acetamide

HRID 2212197

Reaktionsgleichung

Reaktionsgleichung von HRID 2212197
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.Br[CH2:25][C:26]([NH:28][C:29]1[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=1)=[O:27].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[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]([CH2:25][C:26]([NH:28][C:29]4[CH:30]=[C:31]([O:39][CH3:40])[C:32]([O:37][CH3:38])=[C:33]([O:35][CH3:36])[CH:34]=4)=[O:27])[CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 219637112-Bromo-N-(3,4,5-trimethoxy-phenyl)-acetamideHCID 219637129-Chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

Produkt 1

HCID 219637142-[3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidin-1-yl]-N-(3,4,5-trimethoxy-phenyl)-acetamideAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

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-bromo-N-(3,4,5-trimethoxy-phenyl)-acetamide (38 mg, 0.12 mmol), and tetrahydrofuran (3 mL) to a roundbottom flask. Stir and add potassium iodide (2 mg, 0.01 mmol) and potassium carbonate (34 mg, 0.25 mmol) at room temperature under nitrogen overnight. Concentrate the reaction, partitions between water and 20% isopropanol/chloroform, and separate. Was the organic layer with saturated aqueous sodium bicarbonate solution, brine, dry over magnesium sulfate and concentrate. Purify by flash chromatography on silica gel (eluting with 0–0.5% methanol/chloroform) to give 37.6 mg of the title compound as an orange solid, 62% yield. 1H NMR: consistent with structure. MS (ion spray) 541 (M+).

Aufarbeitung

  1. concentrationConcentrate
  2. customthe reaction, partitions between water and 20% isopropanol/chloroform
  3. customseparate
  4. dry with materialdry over magnesium sulfate
  5. concentrationconcentrate
  6. customPurify by flash chromatography on silica gel (eluting with 0–0.5% methanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-fbbecfc0e325409da1c44840f8581115
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101891B2

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