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

HRID 606956노트

반응식

HRID 606956 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 1049Pyridine용매HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-e162a1bfde0440e4a4d47b5a19036340
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915424B2

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