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

HRID 572171ノート

反応式

HRID 572171 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 102360762-Chloro-N-methoxy-N-methylnicotinamide収率 63.4%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-826f12a127f94e3286c682ff320c6886
出典データセット
uspto-grants-2015_05
特許番号
US09029388B2

反応ノート

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