O-Methylhydroxylamine hydrochloride → HCID 85082990, Verbindung

HRID 854828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 854828
[Br:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:29])[CH:10]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[C:20]([Cl:28])[CH:19]=2)[CH2:11][CH:12]2[CH2:16][CH2:15][C:14](=O)[CH2:13]2)=[N:6][CH:7]=1.Cl.[CH3:31][O:32][NH2:33]>CO.N1C=CC=CC=1>[Br:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:29])[CH:10]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:25])=[O:26])=[C:20]([Cl:28])[CH:19]=2)[CH2:11][CH:12]2[CH2:16][CH2:15][C:14](=[N:33][O:32][CH3:31])[CH2:13]2)=[N:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 9983474N-(5-bromo-pyrazin-2-yl)-2-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclopentyl)-propionamide

Produkt 1

HCID 85082990HCID 85082990, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of N-(5-bromo-pyrazin-2-yl)-2-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclopentyl)-propionamide (prepared as in Example 49, 190 mg, 0.38 mmol) and methoxyamine hydrochloride (48 mg, 0.57 mmol) in methanol (0.90 mL) and pyridine (0.90 mL) was heated under reflux for 3 h. The reaction mixture was allowed to cool to 25° C. and then was concentrated in vacuo. The resulting residue was diluted with water (50 mL) and extracted with ethyl acetate (50 mL). The organic layers were washed with a 1N aqueous hydrochloric acid solution (50 mL) and a saturated aqueous sodium chloride solution (50 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 50% ethyl acetate/hexanes) afforded the N-(5-bromo-pyrazin-2-yl)-2-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-methoxyimino-cyclopentyl)-propionamide (61.2 mg, 78%) as a yellow foam: mp 91-97° C.; (ES)+-HRMS m/e calcd for C20H22BrClN4O4S (M+H)+ 529.0307. found 529.0310.

Aufarbeitung

  1. temperatureunder reflux for 3 h
  2. concentrationwas concentrated in vacuo
  3. additionThe resulting residue was diluted with water (50 mL)
  4. extractionextracted with ethyl acetate (50 mL)
  5. washThe organic layers were washed with a 1N aqueous hydrochloric acid solution (50 mL)
  6. dry with materiala saturated aqueous sodium chloride solution (50 mL), dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ef2e85f5c37349208e4f7a1cad3e8248
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259166B2

Notizen zur Reaktion

Wird geladen…