Dimethylformamide → HCID 58951429, Verbindung

HRID 1445755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1445755
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]([C:17]3[O:18][C:19]([CH3:26])=[C:20]([CH2:22][C:23]([O-])=[O:24])[N:21]=3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Na+].[C:28](Cl)(=O)C(Cl)=O.CN(C)C=O.C[N:40]1[CH2:45][CH2:44]O[CH2:42][CH2:41]1>O1CCOCC1.ClCCl>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]([C:17]3[O:18][C:19]([CH3:26])=[C:20]([CH2:22][C:23]([N:40]4[CH2:41][CH2:42][CH2:28][C@H:45]4[CH3:44])=[O:24])[N:21]=3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 65578Oxalyl chlorideHCID 86614632Sodium {2-[6-(4-methanesulfonyl-phenyl)-pyridin-3-yl]-5-methyl-oxazol-4-yl}-acetate2×

Produkt 1

HCID 58951429HCID 58951429, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirring solution of Sodium {2-[6-(4-methanesulfonyl-phenyl)-pyridin-3-yl]-5-methyl-oxazol-4-yl}-acetate (See Intermediate 20) (1.0 mmol) and oxalyl chloride (3.0 mmol) in dioxane (0.10M), add a catalytic amount of dimethylformamide and heat to reflux for 30 minutes. After this time, remove the heat and concentrate in vacuo. Take the resulting solid into dichloromethane (0.10M) and slowly add a solution of (R)-methyl-pyrrolidine hydrochloride (1.0 mmol) and n-methylmorpholine (2.0 mmol) in dichloromethane. Stir at room temperature for 1 hour. After this time, the reaction appears complete. Wash the reaction with 1N hydrochloric acid while extracting with dichloromethane. Concentrate the organic layer in vacuo and purify via radial chromatography eluting with methanol and dichloromethane. MS (m/e): 440.2(M+1)

Aufarbeitung

  1. temperatureheat
  2. temperatureto reflux for 30 minutes
  3. customAfter this time, remove the
  4. temperatureheat
  5. concentrationconcentrate in vacuo
  6. washWash
  7. customthe reaction with 1N hydrochloric acid
  8. extractionwhile extracting with dichloromethane
  9. concentrationConcentrate the organic layer in vacuo
  10. custompurify via radial chromatography
  11. washeluting with methanol and dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-0fe51d26929a4bb588d1a1c741c6a049
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666871B2

Notizen zur Reaktion

Wird geladen…