4-Cyanophenyl isocyanate → (2R,5S)-4'-Cyano-4-(4-cyano-3-fluoro-5-methoxyphenyl)-2,5-dimethylpiperazine-1-carboxanilide

HRID 1445478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1445478
[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][N:3]1[C:9]1[CH:16]=[C:15]([O:17][CH3:18])[C:12]([C:13]#[N:14])=[C:11]([F:19])[CH:10]=1.[N:20]([C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1)=[C:21]=[O:22]>C(#N)C>[C:27]([C:26]1[CH:29]=[CH:30][C:23]([NH:20][C:21]([N:6]2[CH2:7][C@H:2]([CH3:1])[N:3]([C:9]3[CH:16]=[C:15]([O:17][CH3:18])[C:12]([C:13]#[N:14])=[C:11]([F:19])[CH:10]=3)[CH2:4][C@H:5]2[CH3:8])=[O:22])=[CH:24][CH:25]=1)#[N:28]

Komponenten

4

Edukt 2

HCID 1703804-Cyanophenyl isocyanateHCID 686911704-[(2S,5R)-2,5-dimethylpiperazin-1-yl]-2-fluoro-6-methoxybenzonitrile

Produkt 1

HCID 68695786(2R,5S)-4'-Cyano-4-(4-cyano-3-fluoro-5-methoxyphenyl)-2,5-dimethylpiperazine-1-carboxanilideAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Into 20 ml of acetonitrile was dissolved 500 mg of 4-[(2S,5R)-2,5-dimethylpiperazin-1-yl]-2-fluoro-6-methoxybenzonitrile, and then 274 mg of 4-isocyanatobenzonitrile was added thereto, followed by 1 hour of stirring at room temperature. The reaction solution was concentrated, followed by addition of ethyl acetate and filtration. The filtrate was removed by evaporation and the resulting powder was crystallized from hexane-ethyl acetate (85:15, v/v) to obtain 535 mg of the title compound.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated
  2. additionfollowed by addition of ethyl acetate and filtration
  3. customThe filtrate was removed by evaporation
  4. customthe resulting powder was crystallized from hexane-ethyl acetate (85:15, v/v)

Quellen und Nachweise

ORD-Eintrag
ord-4c9f2f89438444b7864fa93af41233db
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666873B2

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