1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Chloro-N-methoxy-N-methylnicotinamide

HRID 572171노트

반응식

HRID 572171 반응식
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH3:12][NH:13][O:14][CH3:15].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(=O)([O-])O.[Na+].C(N(CC)CC)C>[Cl:1][C:2]1[C:7]([C:8]([N:13]([O:14][CH3:15])[CH3:12])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1

참가 물질

8

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 762582-Chloronicotinic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

생성물 1

HCID 102360762-Chloro-N-methoxy-N-methylnicotinamide수율 63.4%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 516892Sodium Bicarbonate용매

실험 절차

2-Chloropyridine-3-carboxylic acid (13 g), N,O-dimethylhydroxylamine hydrochloride (8.85 g), HOBt (5.57 g), EDCI (15.37 g) and triethylamine (34.5 ml) were dissolved in DMF (150 ml), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate) to give the title compound (10.5 g).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-826f12a127f94e3286c682ff320c6886
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029388B2

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