Acetonitrile → [5-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amine

HRID 2080471

반응식

HRID 2080471 반응식
[C:1](#[N:3])[CH3:2].[Cl:4][C:5]1[C:6]([CH:23]([S:32]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])=CC(NCC2C=CC(OC)=C(OC)C=2)=N[CH:10]=1.[N+:42]([O-])([O-])=O.[NH4+].[NH4+].[Ce+4].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.C(=O)(O)[O-].[Na+]>O>[Cl:4][C:5]1[C:6]([CH:23]([S:32]([C:35]2[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=2)(=[O:33])=[O:34])[C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])=[CH:2][C:1]([NH2:42])=[N:3][CH:10]=1

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 516892Sodium BicarbonateHCID 231147515-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-2-(3,4-dimethoxybenzylamino)pyridine

생성물 1

HCID 23114671[5-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amine수율 38%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To an acetonitrile (4 ml)/water (1 ml) mixed solution of the 5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-2-(3,4-dimethoxybenzylamino)pyridine (43 mg, 0.074 mmol) obtained in Example 186 was added cerium (IV) diammonium nitrate (100 mg) under ice cooling. The resulting mixture was stirred for 1.5 hours. To the reaction mixture was added saturated sodium bicarbonate, followed by extraction with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was purified by silica gel thin-layer chromatography (hexane:ethyl acetate=3:1) to give the title compound (12 mg, 0.028 mmol, 38%) as a pale yellowish white powder.

후처리

  1. extractionfollowed by extraction with methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel thin-layer chromatography (hexane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-2ff93e0a106c4ac5bac60f62f77092a8
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932271B2

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