1-Methylpiperazine → 4-[4-ethoxy-3-(trifluoromethyl)phenyl]-7-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

HRID 522292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 522292
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.C(C(=NO[C+](N(C)C)N1CCOCC1)C(OCC)=O)#N.[C:44]([C:46]1[N:47]=[C:48]([C:59]2[CH:64]=[CH:63][C:62]([O:65][CH2:66][CH3:67])=[C:61]([C:68]([F:71])([F:70])[F:69])[CH:60]=2)[C:49]2[CH:54]=[CH:53][N:52]([CH2:55][C:56](O)=[O:57])[C:50]=2[N:51]=1)#[N:45]>O.CN(C=O)C>[CH2:66]([O:65][C:62]1[CH:63]=[CH:64][C:59]([C:48]2[C:49]3[CH:54]=[CH:53][N:52]([CH2:55][C:56]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[O:57])[C:50]=3[N:51]=[C:46]([C:44]#[N:45])[N:47]=2)=[CH:60][C:61]=1[C:68]([F:69])([F:70])[F:71])[CH3:67]

Komponenten

7

Edukt 4

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 90065599{2-cyano-4-[4-ethoxy-3-(trifluoromethyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetic acidHCID 178472143HCID 178472143, Verbindung

Produkt 1

HCID 1178995474-[4-ethoxy-3-(trifluoromethyl)phenyl]-7-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-Methylpiperazine (42 μL), N,N-diisopropylethylamine (66 μL), and (1-cyano-2-ethoxy-2-oxoethylidene aminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate (187 mg) were added to a mixture of {2-cyano-4-[4-ethoxy-3-(trifluoromethyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetic acid (100 mg) and DMF (4 mL) at room temperature, and the mixture was stirred at the same temperature for 2 hours. After water was added to the reaction mixture, the precipitate was collected by filtration, and washed with water. After the obtained solid was dissolved in CHCl3, the solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3:MeOH=100:0 to 50:50), whereby 4-[4-ethoxy-3-(trifluoromethyl)phenyl]-7-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (82 mg) was obtained as a white solid.

Aufarbeitung

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water
  3. dissolutionAfter the obtained solid was dissolved in CHCl3
  4. concentrationthe solution was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (CHCl3:MeOH=100:0 to 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-9fea9a1a8cb64d1797ceb0c09108ed39
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328118B2

Notizen zur Reaktion

Wird geladen…