Triethylamine → 1-(1-(3,6-Dichloropyridazin-4-yl)piperidin-4-yl)ethanone

HRID 454940

반응식

HRID 454940 반응식
C(N(CC)CC)C.[Cl:8][C:9]1[N:10]=[N:11][C:12]([Cl:16])=[CH:13][C:14]=1Cl.[NH:17]1[CH2:22][CH2:21][CH:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH2:18]1>CN(C=O)C.O>[Cl:8][C:9]1[N:10]=[N:11][C:12]([Cl:16])=[CH:13][C:14]=1[N:17]1[CH2:22][CH2:21][CH:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH2:18]1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 951233,4,6-TrichloropyridazineHCID 27237641-(Piperidin-4-yl)ethan-1-one

생성물 1

HCID 585479571-(1-(3,6-Dichloropyridazin-4-yl)piperidin-4-yl)ethanone수율 39%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Triethylamine (2.2 g, 20.0 mmol), 3,4,6-trichloro-pyridazine (1.8 g, 10.0 mmol) and 1-(piperidin-4-yl)ethanone (1.3 g, 10.0 mmol) was dissolved in DMF (20 mL) and the resulting mixture was stirred at room temperature overnight. The mixture was then diluted with water (50 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were combined and washed with water (20 mL) and brine (20 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 50% EtOAc in hexanes) to give 1-(1-(3,6-dichloropyridazin-4-yl)piperidin-4-yl)ethanone (1.0 g, 3.8 mmol, 39% yield) as white solid. ESI-MS (M+1): 274 calc. for C11H13ClN3O 273.

후처리

  1. extractionextracted with EtOAc (2×50 mL)
  2. washwashed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel (20% to 50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-9f93ca938d46472888460804cf7f0d07
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497265B2

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