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HCID 86630875, Verbindung → 4,5-Diamino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-methylbiphenyl-3-carbonitrile

HRID 17554
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17554
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([N:11]2[CH2:15][CH2:14][C@H:13]([N:16]([CH3:18])[CH3:17])[CH2:12]2)[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([CH3:25])[C:3]=1[C:26]#[N:27]>O.O.O.O.O.O.[Fe](Cl)Cl.[Zn].CN(C)C=O>[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([N:11]2[CH2:15][CH2:14][C@H:13]([N:16]([CH3:17])[CH3:18])[CH2:12]2)[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([CH3:25])[C:3]=1[C:26]#[N:27]
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Komponenten

5

Edukt 1

HCID 86630875HCID 86630875, Verbindung

Produkt 1

HCID 866308764,5-Diamino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-methylbiphenyl-3-carbonitrileAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 129819097HCID 129819097, VerbindungKatalysatorHCID 6228Dimethylformamide
Lösungsmittel

Versuchsvorschrift

An aqueous solution (14 ml) of iron chloride hexahydrate (0.83 g, 3.06 mmol) and zinc (5.01 g, 76.6 mmol) were added to an N,N-dimethylformamide (35 ml) solution of 4-amino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-methyl-5-nitrobiphenyl-3-carbonitrile (I-268) (1.40 g, 3.83 mmol), followed by stirring at room temperature for 1 hour. The insoluble matter was removed by filtration under suction, then the filtrate was diluted with ethyl acetate, washed with aqueous saturated sodium carbonate solution and saturated brine in that order, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, followed by drying with a vacuum pump to obtain the entitled compound (1.25 g, 97%) as a dark brown solid.

Aufarbeitung

  1. customThe insoluble matter was removed by filtration under suction
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with aqueous saturated sodium carbonate solution and saturated brine in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customby drying with a vacuum pump

Quellen und Nachweise

ORD-Eintrag
ord-1a0f2bcf5dc94f82a80cbefce8556a45
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737166B2

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