Dimethylformamide → N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-1-methyl-1H-imidazole-4-sulfonamide

HRID 1062756노트

반응식

HRID 1062756 반응식
[H-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]([O:30][CH2:31][CH2:32][OH:33])=[N:14][N:15]([CH3:29])[C:16]=3[NH:17][S:18](/[CH:21]=[CH:22]/C3C=CC=CC=3)(=[O:20])=[O:19])=[CH:11][C:6]=2[O:5][CH2:4]1.[Cl:34][C:35]1[CH:36]=[N:37][C:38](S(C)(=O)=O)=[N:39][CH:40]=1.[Cl-].[NH4+:46].[CH3:47][N:48]([CH3:51])C=O>O>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]([O:30][CH2:31][CH2:32][O:33][C:38]4[N:37]=[CH:36][C:35]([Cl:34])=[CH:40][N:39]=4)=[N:14][N:15]([CH3:29])[C:16]=3[NH:17][S:18]([C:21]3[N:46]=[CH:47][N:48]([CH3:51])[CH:22]=3)(=[O:20])=[O:19])=[CH:11][C:6]=2[O:5][CH2:4]1

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27277255-Chloro-2-methanesulfonylpyrimidineHCID 22281926HCID 22281926, 화합물

생성물 1

HCID 9871777N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-1-methyl-1H-imidazole-4-sulfonamide

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Sodium hydride (60% dispersion in oil, 20 mg) was carefully added to a solution of (E)-N-[4-(1,3-benzodioxol-5-yl)-3-(2-hydroxyethoxy)-1-methyl-1H-pyrazol-5-yl]-2-phenyl-1-ethenesulfonamide (Preparation 44) (100 mg) in anhydrous dimethylformamide (4.4 ml) at room temperature under an atmosphere of nitrogen. After 10 minutes the 5-chloro-2-(methylsulfonyl)pyrimidine (104 mg) was added and the mixture was stirred overnight. To the reaction mixture was then sequentially added an aqueous solution of ammonium chloride (4 ml) and water (30 ml) before being extracted with ether (3×8 ml). Combined organic phases were sequentially washed with water (20 ml), brine (20 ml), dried over magnesium sulfate and concentrated under reduced pressure. A purification by column chromatography (silica, 10 g) eluted with dichloromethane:methanol (95:5) yielded the title compound as a colourless oil (85 mg).

후처리

  1. extractionbefore being extracted with ether (3×8 ml)
  2. washCombined organic phases were sequentially washed with water (20 ml), brine (20 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customA purification by column chromatography (silica, 10 g)
  6. washeluted with dichloromethane:methanol (95:5)

출처 및 근거

ORD 기록
ord-807673e4b4fa4831b455d139c1e02fa3
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06962923B2

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