Sodium hydride → N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1H-pyrazol-5-yl]-N-(methoxymethyl)-2-phenyl-1-ethanesulfonamide

HRID 1062810ノート

反応式

HRID 1062810 の反応式
[H-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]([O:29][CH3:30])=[N:14][NH:15][C:16]=3[NH:17][S:18]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:20])=[O:19])=[CH:11][C:6]=2[O:5][CH2:4]1.[CH3:31][O:32][CH2:33]Br.[Cl-].[NH4+]>O1CCCC1>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]([O:29][CH3:30])=[N:14][NH:15][C:16]=3[N:17]([CH2:31][O:32][CH3:33])[S:18]([CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)(=[O:20])=[O:19])=[CH:11][C:6]=2[O:5][CH2:4]1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 83093Bromomethyl methyl etherHCID 22281999N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1H-pyrazol-5-yl]-2-phenyl-1-ethanesulfonamide

生成物 1

HCID 22282022N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1H-pyrazol-5-yl]-N-(methoxymethyl)-2-phenyl-1-ethanesulfonamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (60% dispersion in oil, 5 mg) was added at room temperature under an atmosphere of nitrogen to a solution of N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1H-pyrazol-5-yl]-2-phenyl-1-ethanesulfonamide (Preparation 56) in anhydrous tetrahydrofuran (2.5 ml). After 10 minutes, bromomethyl methyl ether (12 μl) was added and the reaction was stirred overnight. An aqueous saturated solution of ammonium chloride (4 ml) was added and the mixture was extracted with ethyl acetate (3×6 ml). The combined organic fractions were washed with brine (6 ml), dried over sodium sulfate and concentrated under reduced pressure. The oily residue was purified by column chromatography (Sep-Pak)™ eluted with hexane:ethyl acetate (4:1) then with hexane:ethyl acetate (1:1) to yield the title compound as a white solid (40 mg).

後処理

  1. extractionthe mixture was extracted with ethyl acetate (3×6 ml)
  2. washThe combined organic fractions were washed with brine (6 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe oily residue was purified by column chromatography (Sep-Pak)™
  6. washeluted with hexane:ethyl acetate (4:1)

出典と根拠

ORDレコード
ord-3ea6cc31515b444298029fbb7036b166
出典データセット
uspto-grants-2005_11
特許番号
US06962923B2

反応ノート

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