Potassium Carbonate → 5-Chloro-1-[3-chloro-5-(methylsulfonyl)benzyl]-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride

HRID 447821ノート

反応式

HRID 447821 の反応式
[C:1]([CH:3]([CH:7]1[C:11]([Cl:12])=[C:10](Cl)C(=O)O1)[C:4]([NH2:6])=[O:5])#[N:2].Cl.[Cl:16][C:17]1[CH:18]=[C:19]([CH2:27][NH2:28])[CH:20]=[C:21]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:22]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>C(O)C>[ClH:12].[Cl:12][C:11]1[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:1](=[NH:2])[N:28]([CH2:27][C:19]2[CH:20]=[C:21]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:22]=[C:17]([Cl:16])[CH:18]=2)[CH:10]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 66877784(3-Chloro-5-methanesulfonylphenyl)methanamine hydrochloride

生成物 1

HCID 669702215-Chloro-1-[3-chloro-5-(methylsulfonyl)benzyl]-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride収率 42.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

(Step 4) 2-Cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (1.68 g), 1-[3-chloro-5-(methylsulfonyl)phenyl]methanamine hydrochloride obtained in Step 3 (2.2 g) and potassium carbonate (2.97 g) were stirred in ethanol (30 ml) at 85° C. for 24 hr. The reaction mixture was treated with 1N sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate). The obtained residue was dissolved in methanol, and 4N hydrogen chloride-ethyl acetate solution (3 ml) was added. The mixture was crystallized from methanol-ethyl acetate, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (0.63 g).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (ethyl acetate)
  6. dissolutionThe obtained residue was dissolved in methanol
  7. addition4N hydrogen chloride-ethyl acetate solution (3 ml) was added
  8. customThe mixture was crystallized from methanol-ethyl acetate
  9. filtrationthe precipitated crystals were collected by filtration
  10. customrecrystallized

出典と根拠

ORDレコード
ord-3451cf6b87ff4f138f004eba6f7a3164
出典データセット
uspto-grants-2013_07
特許番号
US08481569B2

反応ノート

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