4-Chloro-2-methylpyridine hydrochloride → HCID 66805338、化合物

HRID 1193350ノート

反応式

HRID 1193350 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

HCID 66805338HCID 66805338、化合物収率 51%

試薬・触媒・溶媒 3

HCID 3776Isopropanol溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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%

後処理

  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)

出典と根拠

ORDレコード
ord-749c85f60e9e44dca116dd0ffefe3af8
出典データセット
uspto-grants-2014_03
特許番号
US08680159B2

反応ノート

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