Ethanesulfonyl chloride → N-(4-(2,4-difluorophenoxy)-3-(6-methyl-7-oxo-1-tosyl-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl)-N-(ethylsulfonyl)ethanesulfonamide

HRID 930860ノート

反応式

HRID 930860 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=2[F:37])=[C:6]([C:8]2[C:9]3[CH:18]=[CH:17][N:16]([S:19]([C:22]4[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:7]=1.[CH2:38]([S:40](Cl)(=[O:42])=[O:41])[CH3:39]>ClCCl>[F:37][C:31]1[CH:32]=[C:33]([F:36])[CH:34]=[CH:35][C:30]=1[O:29][C:5]1[CH:4]=[CH:3][C:2]([N:1]([S:19]([CH2:22][CH3:23])(=[O:21])=[O:20])[S:40]([CH2:38][CH3:39])(=[O:42])=[O:41])=[CH:7][C:6]=1[C:8]1[C:9]2[CH:18]=[CH:17][N:16]([S:19]([C:22]3[CH:23]=[CH:24][C:25]([CH3:26])=[CH:27][CH:28]=3)(=[O:20])=[O:21])[C:10]=2[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=1

参加物

4

反応物 2

HCID 11667Ethanesulfonyl chlorideHCID 89657311HCID 89657311、化合物

生成物 1

HCID 89657386N-(4-(2,4-difluorophenoxy)-3-(6-methyl-7-oxo-1-tosyl-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl)-N-(ethylsulfonyl)ethanesulfonamide収率 181.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of Example 36c (4.35 g, 8.34 mmol) in dichloromethane (50 mL) was cooled to 0° C. To this solution was added ethanesulfonyl chloride (2.37 mL, 25.0 mmol). The reaction mixture was stirred at room temperature for 2 hours. The solvent was evaporated, and the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 80% ethyl acetate/hexanes) to provide the title compound (5.34 g, 91% yield).

後処理

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with additional ethyl acetate twice
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (silica gel, 80% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-6ffc960bec824453b3d20bbdd401c573
出典データセット
uspto-grants-2016_03
特許番号
US09296741B2

反応ノート

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