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

Reaktionsgleichung

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

Edukt 3

HCID 8028Tetrahydrofuran

HCID 199374482H-1,2-Benzoxazin-3(4H)-one

HCID 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.