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

HRID 988731

反応式

HRID 988731 の反応式
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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f9c8d6f0cb794452a058e0cb236c41b8
出典データセット
uspto-grants-2003_10
特許番号
US06635657B1

関連ノート

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