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Chloroform → N-[4-Amino-5-cyano-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methylbiphenyl-3-yl]-2,2-dimethylpropionamide

HRID 17555
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17555
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(Cl)(Cl)Cl.[NH2:12][C:13]1[C:18]([NH2:19])=[C:17]([N:20]2[CH2:24][CH2:23][C@H:22]([N:25]([CH3:27])[CH3:26])[CH2:21]2)[C:16]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:15]([CH3:34])[C:14]=1[C:35]#[N:36]>O>[NH2:12][C:13]1[C:14]([C:35]#[N:36])=[C:15]([CH3:34])[C:16]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[C:17]([N:20]2[CH2:24][CH2:23][C@H:22]([N:25]([CH3:27])[CH3:26])[CH2:21]2)[C:18]=1[NH:19][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]
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Komponenten

5

Edukt 3

HCID 6212ChloroformHCID 62493Pivaloyl chlorideHCID 866308764,5-Diamino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-methylbiphenyl-3-carbonitrile

Produkt 1

HCID 86630877N-[4-Amino-5-cyano-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methylbiphenyl-3-yl]-2,2-dimethylpropionamideAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

With cooling with ice, pivaloyl chloride (0.46 ml, 3.73 mmol) was dropwise added to a chloroform (40 ml) solution of 4,5-diamino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-methylbiphenyl-3-carbonitrile (I-269) (1.25 g, 3.73 mmol). After stirring for 3 hours, water was added to the reaction liquid to stop the reaction, followed by extraction with chloroform. The organic layer was washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine, then dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, then the residue was subjected to column chromatography, and eluted with a mixed solvent of chloroform/methanol (95:5, v/v) to obtain the entitled compound (675 mg, 43%) as a brown amorphous substance.

Aufarbeitung

  1. customthe reaction
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. washeluted with a mixed solvent of chloroform/methanol (95:5

Quellen und Nachweise

ORD-Eintrag
ord-3ec1a66659864c1384b987eaee51beef
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737166B2

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