4-Chloro-2-methylpyridine hydrochloride → HCID 66805338, 화합물

HRID 1193350노트

반응식

HRID 1193350 반응식
[C:1]([N:8]([CH3:13])[CH:9]1[CH2:12][NH:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.Cl[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([CH3:22])[CH:17]=1>CC(O)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH3:13][N:8]([CH:9]1[CH2:12][N:11]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([CH3:22])[CH:17]=2)[CH2:10]1)[C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5]

참가 물질

6

반응물 2

HCID 27628414-Chloro-2-methylpyridine hydrochlorideHCID 23033645tert-Butyl azetidin-3-yl(methyl)carbamate

생성물 1

HCID 66805338HCID 66805338, 화합물수율 51%

시약·촉매·용매 3

HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

3-(Boc-methylamino)azetidine (2.74 mmol, 1.0 eq) and 4-chloro-2-methylpyridine HCl (8.21 mmol, 3.0 eq) were dissolved in 2-propanol (5 ml) and DI PEA (13.69 mmol. 5.0 eq) and refluxed for 24 hours. After monitoring by TLC, the reaction solution was diluted with ethyl acetate and sat. sodium hydrogen carbonate solution, and the phases were separated. The aqueous phase was washed with ethyl acetate. The combined organic phases were washed 1× with sat. NaCl solution, dried over magnesium sulfate, concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, ethyl acetate:ethanol 10:1+ammonia solution). Yield: 51%

후처리

  1. temperatureDI PEA (13.69 mmol. 5.0 eq) and refluxed for 24 hours
  2. customthe phases were separated
  3. washThe aqueous phase was washed with ethyl acetate
  4. washThe combined organic phases were washed 1× with sat. NaCl solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (silica gel, ethyl acetate:ethanol 10:1+ammonia solution)

출처 및 근거

ORD 기록
ord-749c85f60e9e44dca116dd0ffefe3af8
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680159B2

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