Methanesulfonyl chloride → N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorophenyl]-methanesulfonamide

HRID 606956ノート

反応式

HRID 606956 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH:18]=2)[C:16]#[N:17])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:19][S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1.O1CCCC1.O>[C:16]([C:15]1[CH:18]=[C:11]([C:10]#[C:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([NH:1][S:20]([CH3:19])(=[O:22])=[O:21])[CH:3]=2)[CH:12]=[N:13][CH:14]=1)#[N:17]

参加物

6

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 670478225-(3-Amino-4-fluorophenylethynyl)-nicotinonitrile

生成物 1

HCID 67047582N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorophenyl]-methanesulfonamide収率 20%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Dissolve 5-(3-amino-4-fluorophenylethynyl)-nicotinonitrile, (prepared as described in EXAMPLE 160), (0.2 g, 0.8 mmol) in anhydrous pyridine. Add a solution of methanesulfonyl chloride (0.1 g, 0.88 mmol) in tetrahydrofuran to the reaction and stir overnight at room temperature. Concentrate and dissolve the crude reaction in ethyl acetate and water. Wash the organic layer with water, an aqueous saturated solution of sodium chloride, dry (potassium carbonate), filter, concentrate and purify (silica gel chromatography, eluting with 95:5 to 80:20 dichloromethane:ethyl acetate), to give the title compound as a tan solid (50 mg, 20%).

後処理

  1. customto the reaction
  2. concentrationConcentrate
  3. dissolutiondissolve the crude
  4. customreaction in ethyl acetate
  5. washWash the organic layer with water
  6. dry with materialan aqueous saturated solution of sodium chloride, dry (potassium carbonate)
  7. filtrationfilter
  8. concentrationconcentrate
  9. custompurify
  10. wash(silica gel chromatography, eluting with 95:5 to 80:20 dichloromethane:ethyl acetate)

出典と根拠

ORDレコード
ord-e162a1bfde0440e4a4d47b5a19036340
出典データセット
uspto-grants-2011_03
特許番号
US07915424B2

反応ノート

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