Sodium Iodide → 3-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-(1-cyano-1-cyclopropylethyl)benzamide

HRID 1878438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1878438
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[F:16].Cl[CH2:18][C:19]1[CH:20]=[C:21]([CH:32]=[CH:33][CH:34]=1)[C:22]([NH:24][C:25]([C:30]#[N:31])([CH:27]1[CH2:29][CH2:28]1)[CH3:26])=[O:23].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:11][CH2:12][N:13]([CH2:18][C:19]3[CH:20]=[C:21]([CH:32]=[CH:33][CH:34]=3)[C:22]([NH:24][C:25]([C:30]#[N:31])([CH:27]3[CH2:29][CH2:28]3)[CH3:26])=[O:23])[CH2:14][CH2:15]2)=[O:9])=[CH:4][C:3]=1[F:16]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 63187976(4-Amino-3-fluorophenyl)(piperazin-1-yl)methanoneHCID 66878470HCID 66878470, Verbindung

Produkt 1

HCID 579176753-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-(1-cyano-1-cyclopropylethyl)benzamideAusbeute 15,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(4-Amino-3-fluorophenyl)(piperazin-1-yl)methanone (2.74 mmol, 0.612 g), 3-(chloromethyl)-N-(1-cyano-1-cyclopropylethyl)benzamide (2.74 mmol, 0.72 g), sodium iodide (0.548 mmol, 0.082 g) and potassium carbonate (8.22 mmol, 1.136 g) were combined in acetonitrile (25 mL) and heated to reflux for 2 hours. The reaction was concentrated under reduced pressure and the resulting residue taken up in dichloromethane and washed with water. The organic phase was dried over sodium sulfate and concentrated under vacuum. The residue was purified by silica column chromatography (eluting with dichloromethane to 4% methanol/dichloromethane) to afford the title compound (195 mg). MS (ESI) m/z 450.3 [M+H]+

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction was concentrated under reduced pressure
  4. washwashed with water
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by silica column chromatography (eluting with dichloromethane to 4% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-152cba8e56a9490eb5b0a956bdb1b975
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314091B2

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