Chloroacetone → 2,6-Dimethylimidazo[1,2-b]pyridazine

HRID 226023노트

반응식

HRID 226023 반응식
[NH2:1][C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.Cl[CH2:10][C:11](=O)[CH3:12].C([O-])(O)=O.[Na+]>CCO>[CH3:12][C:11]1[N:1]=[C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[N:4][N:3]2[CH:10]=1

참가 물질

5

반응물 3

HCID 6571ChloroacetoneHCID 877126-Methylpyridazin-3-amineHCID 516892Sodium Bicarbonate

생성물 1

HCID 218176672,6-Dimethylimidazo[1,2-b]pyridazine수율 51%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 3-amino-6-methyl-pyridazine (4.53 g, 41.58 mmol) in EtOH (60 mL) is treated with chloroacetone (3.5 mL, 43.66 mmol). The reaction is refluxed overnight. While it is hot, NaHCO3 (8.7 g, 103.9 mmol) is added in portions. The resulting mixture is refluxed for 2 h. It is cooled to rt and filtered through silical gel, washed with EtOAc, and concentrated. Purification of the crude material by chromatography gives the title compound (3.1 g, 21.11 mmol, 51%). 1H NMR (CDCl3): δ 2.49 (s, 3H), 2.55 (s, 3H), 6.84 (d, J=9.3 Hz, 1H), 7.64 (s, 1H), 7.70 (d, J=9.3 Hz, 1H) ppm. ES-MS (m/z): calcd for C8H9N3 (M+H)+: 148.2. found: 148.1.

후처리

  1. temperatureThe reaction is refluxed overnight
  2. temperatureThe resulting mixture is refluxed for 2 h
  3. filtrationfiltered through silical gel
  4. washwashed with EtOAc
  5. concentrationconcentrated
  6. customPurification of the crude material by chromatography

출처 및 근거

ORD 기록
ord-d8c34bddadeb48b6a48b90880cda2565
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557103B2

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