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Acetonitrile → HCID 46869255、化合物

HRID 474430
ノート
印刷プレビュー

反応式

HRID 474430 の反応式
[CH2:1]([N:3](S(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O)[CH2:4][C@@H:5]([NH:12][C:13]1[C:22]2[C:17](=[C:18]([C:23]([NH2:25])=[O:24])[CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:2].C(#N)C.C(=O)([O-])[O-].[Cs+].[Cs+].C1(S)C=CC=CC=1>[NH4+].[Cl-]>[CH2:1]([NH:3][CH2:4][C@@H:5]([NH:12][C:13]1[C:22]2[C:17](=[C:18]([C:23]([NH2:25])=[O:24])[CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 7969ThiophenolHCID 10796Cesium carbonateHCID 66763582HCID 66763582、化合物

生成物 1

HCID 46869255HCID 46869255、化合物収率 21%

試薬・触媒・溶媒 1

HCID 25517Ammonium Chloride溶媒

実験手順

To a 40-mL vial with magnetic stirbar at 25° C. under a nitrogen atmosphere was added 4-{(S)-2-[Ethyl-(4-nitro-benzenesulfonyl)-amino]-1-phenyl-ethylamino}-quinazoline-8-carboxylic acid amide (0.45 g, 0.86 mmol, 1 eq.) and anhydrous acetonitrile (25 mL). The Cesium carbonate (0.84 g, 2.6 mmol, 3 eq.) was added followed by the thiophenol (0.14 g, 1.3 mmol, 0.13 mL, 1.5 eq.). Stirring was continued at 25° C.×16 hours. The reaction mixture was diluted with saturated aqueous NH4Cl solution (40 mL) and extracted with EtOAc (30 mL)×3. The combined organics were washed with brine (20 mL), dried (e.g., Na2SO4), filtered and concentrated. The resulting residue was purified by column chromatography (ISCO CombiFlash) using a 0-100% gradient (10% MeOH in EtOAc/EtOAc) to afford 58.3 mg (21% yield). LCMS (ESI) 336.2 (M+H).

後処理

  1. customwas continued at 25° C.
  2. custom×16 hours
  3. extractionextracted with EtOAc (30 mL)×3
  4. washThe combined organics were washed with brine (20 mL)
  5. dry with materialdried (e.g., Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by column chromatography (ISCO CombiFlash)
  9. customto afford 58.3 mg (21% yield)

出典と根拠

ORDレコード
ord-8978c0b87d0e48499181a4a6d80c07a6
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08637532B2

反応ノート

読み込み中…

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