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Ethyl Acetate → 5-Chloro-1-[4-chloro-3-(methylsulfonyl)benzyl]-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride

HRID 1015731
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HRID 1015731 반응식
[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].Br[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:15]=1.C(OCC)(=O)C>CN(C=O)C>[ClH:11].[Cl:11][C:8]1[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:2](=[NH:1])[N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:15]=2)[CH:9]=1
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참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 668768832-Amino-5-chloronicotinamideHCID 668774604-(Bromomethyl)-1-chloro-2-(methylsulfonyl)benzene

생성물 1

HCID 669700925-Chloro-1-[4-chloro-3-(methylsulfonyl)benzyl]-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride수율 27.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(Step 2) A solution of 2-amino-5-chloronicotinamide (484 mg) and 4-(bromomethyl)-1-chloro-2-(methylsulfonyl)benzene obtained in Step 1 (1.2 g) in DMF (10 ml) was stirred at 90° C. for 20 hr. The mixture was allowed to cool to room temperature, ethyl acetate was added, and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in 1N sodium hydroxide solution, and the solution was 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 yellow solid was dissolved in methanol, 4N hydrogen chloride-ethyl acetate solution (2 ml) was added, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (160 mg).

후처리

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

출처 및 근거

ORD 기록
ord-cc1742f590da4d21b8ed5051c41a03a5
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07985862B2

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