1,1'-Carbonyldiimidazole → N-[methyl(oxo)phenyl-lambda6-sulfanylidene]-5-(phenylethynyl)nicotinamide

HRID 391510

반응식

HRID 391510 반응식
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:17]=2)[C:14]([OH:16])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:30][S@:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[NH:33])=[O:32]>C1COCC1>[CH3:30][S:31](=[O:32])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[N:33][C:14](=[O:16])[C:13]1[CH:17]=[C:9]([C:8]#[C:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:10]=[N:11][CH:12]=1

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27792365-(2-Phenyleth-1-Ynyl)Nicotinic AcidHCID 25036288(S)-(+)-S-Methyl-S-phenylsulfoximine2회

생성물 1

HCID 2822405N-[methyl(oxo)phenyl-lambda6-sulfanylidene]-5-(phenylethynyl)nicotinamide수율 56%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
50 °C

실험 절차

To a slurry of 5-(2-phenyleth-1-ynyl)nicotinic acid (339 mg, 1.5 mmol) in 6.0 mL THF at room temperature was added 1,1′-carbonyldiimidazole (271 mg, 1.7 mmol). After stirring 1.25 hour, a solution of (S)-(+)-S-methyl-S-phenylsulfoximine (260 mg, 1.7 mmol) in 1.5 mL THF was added and the mixture heated at 50° C. for 22 hours. Then an additional 50 mg (0.32 mmol) (S)-(+)-S-methyl-S-phenylsulfoximine was added and heating continued at 60° C. for 3.5 hours. The reaction was quenched with NaHCO3 solution and then extracted into EtOAc. The EtOAc layer was washed with NaHCO3 solution, H2O, brine, dried with anhydrous Na2SO4 and concentrated. The yellow oil obtained was chromatographed eluting with hexane/EtOAc to give N-[methyl(oxo)phenyl-λ6-sulfanylidene]-5-(phenylethynyl)nicotinamide as a white foam (303 mg, 55%).

후처리

  1. temperatureheating
  2. waitcontinued at 60° C. for 3.5 hours
  3. customThe reaction was quenched with NaHCO3 solution
  4. extractionextracted into EtOAc
  5. washThe EtOAc layer was washed with NaHCO3 solution, H2O, brine
  6. dry with materialdried with anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe yellow oil obtained
  9. customwas chromatographed
  10. washeluting with hexane/EtOAc

출처 및 근거

ORD 기록
ord-b6735c799eee440db8eae84f1f4af96f
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383825B2

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