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

HRID 1013959노트

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HRID 1013959 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
70 °C

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-2f750f20cd7b46fcbcfdd5f66699c64c
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07982044B2

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