Trifluoroacetic acid → 6-Chloro-2-cyclopropylimidazo[1,2-b]pyridazine-3-carbaldehyde

HRID 1896408노트

반응식

HRID 1896408 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH:11]3[CH2:13][CH2:12]3)[N:10]=2)[N:7]=1.FC(F)(F)[C:16](O)=[O:17]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:16]=[O:17])=[C:9]([CH:11]3[CH2:13][CH2:12]3)[N:10]=2)[N:7]=1

참가 물질

3

반응물 2

HCID 6422Trifluoroacetic acidHCID 536291716-Chloro-2-cyclopropylimidazo[1,2-b]pyridazine

생성물 1

HCID 577430506-Chloro-2-cyclopropylimidazo[1,2-b]pyridazine-3-carbaldehyde수율 45%

실험 절차

6-chloro-2-cyclopropylimidazo[1,2-b]pyridazine x105 (1.88 g, 9.71 mmol) and hexamethyltetramine (HMTE, 13.61 g, 97.09 mmol, 10 eq) in trifluoroacetic acid (75 ml) are heated at 60° C. during 6 days. After cooling and solvent evaporation under reduced pressure, the crude product is dissolved in dichloromethane (150 ml). The organic layer is washed with water (150 ml) and the resulting aqueous layer is extracted with dichloromethane (150 ml). The cumulated organic layers are dried over MgSO4, filtered and the solvent is removed by evaporation under reduced pressure. The resulting crude compound is purified by preparative chromatography (benzine/AcOEt: 80/20) affording 0.82 g of 6-chloro-2-cyclopropylimidazo[1,2-b]pyridazine-3-carbaldehyde x110.

후처리

  1. temperatureAfter cooling
  2. customsolvent evaporation under reduced pressure
  3. dissolutionthe crude product is dissolved in dichloromethane (150 ml)
  4. washThe organic layer is washed with water (150 ml)
  5. extractionthe resulting aqueous layer is extracted with dichloromethane (150 ml)
  6. dry with materialThe cumulated organic layers are dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent is removed by evaporation under reduced pressure
  9. customThe resulting crude compound is purified by preparative chromatography (benzine/AcOEt: 80/20)

출처 및 근거

ORD 기록
ord-6d022b428d1b4ffb8f2693c6392231eb
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518943B2

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