Pyridine → N-[5-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]-1-methyl-1H-imidazole-4-sulfonamide

HRID 2080517ノート

反応式

HRID 2080517 の反応式
C(Cl)Cl.[Cl:4][C:5]1[C:6]([CH:12]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[CH:7][C:8]([NH2:11])=[N:9][CH:10]=1.N1C=CC=CC=1.[CH3:37][N:38]1[CH:42]=[C:41]([S:43](Cl)(=[O:45])=[O:44])[N:40]=[CH:39]1>CO.C(OCC)(=O)C>[Cl:4][C:5]1[C:6]([CH:12]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[CH:7][C:8]([NH:11][S:43]([C:41]2[N:40]=[CH:39][N:38]([CH3:37])[CH:42]=2)(=[O:45])=[O:44])=[N:9][CH:10]=1

参加物

7

反応物 4

HCID 1049Pyridine2 回HCID 6344DichloromethaneHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 23114671[5-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amine

生成物 1

HCID 23114851N-[5-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]-1-methyl-1H-imidazole-4-sulfonamide収率 55%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a methylene chloride (5 ml) solution of the [5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amine (93 mg, 0.217 mmol) obtained in Example 196 and pyridine (21 μl, 0.260 mmol) was added 1-methyl-1H-imidazole-4-sulfonyl chloride (47 mg, 0.260 mmol). The resulting mixture was stirred at room temperature for 18 hours. After pyridine (1 ml) was added to the reaction mixture and the resulting mixture was stirred at room temperature for 7 hours, the reaction mixture was concentrated under reduced pressure. To the residue thus obtained was added ethyl acetate. The resulting mixture was washed sequentially with a saturated aqueous solution of sodium bicarbonate and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography. The fraction obtained from the methanol:methylene chloride (=1:50) eluate was concentrated under reduced pressure to yield a white solid. The resulting white solid was washed with ethanol, and collected by filtration to give the title compound (68 mg, 0.119 mmol, 55%) as a white powder.

後処理

  1. stirringthe resulting mixture was stirred at room temperature for 7 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customTo the residue thus obtained
  4. washThe resulting mixture was washed sequentially with a saturated aqueous solution of sodium bicarbonate and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue thus obtained
  9. concentrationmethylene chloride (=1:50) eluate was concentrated under reduced pressure
  10. customto yield a white solid
  11. washThe resulting white solid was washed with ethanol
  12. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-1cb600da3d6c4a748411b579efb54cd0
出典データセット
uspto-grants-2011_04
特許番号
US07932271B2

反応ノート

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