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

HRID 1013959ノート

反応式

HRID 1013959 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].[NH2:15][CH2:16][C:17]1[CH:18]=[C:19]([S:23]([NH:26][CH3:27])(=[O:25])=[O:24])[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>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:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([S:23](=[O:25])(=[O:24])[NH:26][CH3:27])[CH:18]=2)[CH:10]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 167855973-(Aminomethyl)-N-methylbenzene-1-sulfonamide

生成物 1

HCID 669698995-Chloro-2-imino-1-[3-(methylsulfamoyl)benzyl]-1,2-dihydropyridine-3-carboxamide hydrochloride収率 32.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

(Step 2) To a suspension of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.28 g) and 3-(aminomethyl)-N-methylbenzenesulfonamide obtained in Step 1 (0.36 g) in ethanol (10 ml) was added potassium carbonate (0.25 g) at room temperature, and the mixture was stirred overnight at 70° C. The reaction solution was filtered through celite. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0). 4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (76 mg).

後処理

  1. filtrationThe reaction solution was filtered through celite
  2. customThe solvent was evaporated under reduced pressure
  3. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0)
  4. addition4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil
  5. filtrationthe precipitated crystals were collected by filtration
  6. customrecrystallized

出典と根拠

ORDレコード
ord-2f750f20cd7b46fcbcfdd5f66699c64c
出典データセット
uspto-grants-2011_07
特許番号
US07982044B2

反応ノート

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