Tetrahydrofuran → 2-(4-tert-Butylbenzoylamino)-N-(5-chloropyridin-2-yl)-5-methoxycarbonylbenzamide

HRID 988731

Reaktionsgleichung

Reaktionsgleichung von HRID 988731
O1C2C=CC=CC=2C[C:3](=[O:11])N1.[C:12]([C:16]1[CH:44]=[CH:43][C:19]([C:20]([NH:22][C:23]2[CH:38]=[C:37](C(OC)=O)[CH:36]=[CH:35][C:24]=2[C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][N:29]=2)=[O:26])=[O:21])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].C1C[O:48][CH2:47]C1>>[C:12]([C:16]1[CH:44]=[CH:43][C:19]([C:20]([NH:22][C:23]2[CH:38]=[CH:37][C:36]([C:47]([O:11][CH3:3])=[O:48])=[CH:35][C:24]=2[C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][N:29]=2)=[O:26])=[O:21])=[CH:18][CH:17]=1)([CH3:15])([CH3:13])[CH3:14]

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 199374482H-1,2-Benzoxazin-3(4H)-oneHCID 219065092-(4-tert-Butylbenzoylamino)-N-(5-chloropyridin-2-yl)-4-methoxycarbonylbenzamide

Produkt 1

HCID 219063172-(4-tert-Butylbenzoylamino)-N-(5-chloropyridin-2-yl)-5-methoxycarbonylbenzamideAusbeute 39 %

Versuchsvorschrift

Into 25 mL THF was dissolved 0.174 g (0.5 mmol) of the above benzoxazinone intermediate. The solution was cooled in an ice bath and placed under nitrogen atmosphere. To the mixture was added 1.5 mL (0.6 mmol) of a 0.4 M solution of the magnesium salt of 2-amino-5-chloropyridine (See Prep. D, Example 278). After 30 min, an additional 1.5 mL (0.6 mmol) of the magnesium salt was added. Stirring was continued for 15 min, and the reaction mixture was quenched with 100 mL cold dilute HCl. The mixture was extracted with 100 mL EtOAc, and the organic layer was washed with 100 mL cold dilute HCl, dried (MgSO4), and concentrated under vacuum. The crude product was chromatographed over silica (0 to 30% EtOAc in hexane gradient), giving 91 mg (39%) of title compound as a crystalline solid.

Aufarbeitung

  1. temperatureThe solution was cooled in an ice bath
  2. waitwas continued for 15 min
  3. customthe reaction mixture was quenched with 100 mL cold dilute HCl
  4. extractionThe mixture was extracted with 100 mL EtOAc
  5. washthe organic layer was washed with 100 mL cold dilute HCl
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under vacuum
  8. customThe crude product was chromatographed over silica (0 to 30% EtOAc in hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-f9c8d6f0cb794452a058e0cb236c41b8
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06635657B1

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