Sodium Iodide → HCID 57917701, Verbindung

HRID 1878387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1878387
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][NH:13][C@@H:12]([CH:16]([CH3:18])[CH3:17])[CH2:11]2)=[O:9])=[CH:4][C:3]=1[F:19].[C:20]([NH:24][C:25](=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32]Cl)[CH:27]=1)([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:32][C:28]3[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=3)[C:25]([NH:24][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:34])[C@@H:12]([CH:16]([CH3:17])[CH3:18])[CH2:11]2)=[O:9])=[CH:4][C:3]=1[F:19]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 43156221N-tert-butyl-3-(chloromethyl)benzamideHCID 57917636HCID 57917636, Verbindung

Produkt 1

HCID 57917701HCID 57917701, VerbindungAusbeute 46,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(S)-(4-Amino-3-fluorophenyl)(3-isopropylpiperazin-1-yl)methanone (0.754 mmol, 200 mg), N-tert-butyl-3-(chloromethyl)benzamide (0,754 mmol, 170 mg), potassium carbonate (1.508 mmol, 208 mg) and sodium iodide (0.075 mmol, 11.30 mg) were dissolved in acetonitrile (20 mL) and heated at reflux for 3 hours. The reaction was concentrated under vacuum and the crude material dissolved in ethyl acetate and washed with water, dried over sodium sulphate and concentration under vacuum. The crude residue was then purified by column chromatography (eluting with dichloromethane to dichloromethane/methanol (1% to 5%)) to give the title compound (160 mg) as an off white solid. MS (ESI) m/z 456.4 [M+H]+

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction was concentrated under vacuum
  4. dissolutionthe crude material dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried over sodium sulphate and concentration under vacuum
  7. customThe crude residue was then purified by column chromatography (eluting with dichloromethane to dichloromethane/methanol (1% to 5%))

Quellen und Nachweise

ORD-Eintrag
ord-57502aaec10d45c281ba2c3cfd853e7c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314091B2

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