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

HRID 391510

反応式

HRID 391510 の反応式
[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

参加物

5

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27792365-(2-Phenyleth-1-Ynyl)Nicotinic AcidHCID 25036288(S)-(+)-S-Methyl-S-phenylsulfoximine2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b6735c799eee440db8eae84f1f4af96f
出典データセット
uspto-grants-2013_02
特許番号
US08383825B2

関連ノート

読み込み中…