5-Chloropentanesulfonamide → 6-(5-Sulfamoylpentylthio)imidazo[1,2-b]pyridazine

HRID 1590063노트

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HRID 1590063 반응식
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7]([NH2:10])(=[O:9])=[O:8].[SH-:11].[K+].C(O)C.C[O-].[Na+].CO.Cl[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]2[N:28]=[CH:29][CH2:30][N:23]12>CO>[S:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][S:11][C:27]1[CH:26]=[CH:25][C:24]2[N:23]([CH:30]=[CH:29][N:28]=2)[N:22]=1)(=[O:9])(=[O:8])[NH2:10]

참가 물질

6

반응물 4

HCID 99899625-ChloropentanesulfonamideHCID 216425665-Chloroimidazo[1,2-b]pyridazineHCID 23694274Sodium methanolate methanolHCID 86746191Potassium hydrosulfide ethanol

생성물 1

HCID 103574626-(5-Sulfamoylpentylthio)imidazo[1,2-b]pyridazine

시약·촉매·용매 1

HCID 887Methanol용매

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온도
70 °C

실험 절차

To a solution of 1.57 g of 5-chloropentanesulfonamide in 40 ml of methanol was added 40 ml of 2N-potassium hydrosulfide-ethanol solution, followed by heating at 70° C. for 45 minutes. To the reaction mixture was added 1.54 g of 28% sodium methoxide-methanol solution and 1.16 g of 5-chloroimidazo[1,2-b]pyridazine, which was refluxed for an hour. The reaction mixture was concentrated to dryness under reduced pressure. The residue was extracted with 40 ml of chloroform and 40 ml of 0.1N-hydrochloric acid. The aqueous layer was extracted three times with chloroform. Then the combined organic layers were dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was subjected to a silica gel column chromatography, eluting with methanol-chloroform (1:35). The corresponding fractions were concentrated. The residue was recrystallized from methanol to obtain 0.62 g of the title compound.

후처리

  1. temperaturewas refluxed for an hour
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  3. extractionThe residue was extracted with 40 ml of chloroform and 40 ml of 0.1N-hydrochloric acid
  4. extractionThe aqueous layer was extracted three times with chloroform
  5. dry with materialThen the combined organic layers were dried over anhydrous magnesium sulfate
  6. distillationdistilled
  7. customto remove the solvent
  8. washeluting with methanol-chloroform (1:35)
  9. concentrationThe corresponding fractions were concentrated
  10. customThe residue was recrystallized from methanol

출처 및 근거

ORD 기록
ord-069aa932f01242499cec7453badbe086
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05202324

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