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

HRID 1883080Notes

Reaction equation

HRID 1883080 reaction equation
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].Cl.C1C[O:49][CH2:48]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:48]([O:11][CH3:3])=[O:49])=[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]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 199374482H-1,2-Benzoxazin-3(4H)-oneHCID 219065092-(4-tert-Butylbenzoylamino)-N-(5-chloropyridin-2-yl)-4-methoxycarbonylbenzamide

Product 1

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

Procedure

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 quinched 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.

Workup

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

Sources & evidence

ORD record
ord-a997ad4193044ac99324ebbb26a6638b
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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