Diisopropylethylamine → US9296748, III-1

HRID 930533

Reaktionsgleichung

Reaktionsgleichung von HRID 930533
CCN(C(C)C)C(C)C.[CH3:10][N:11]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18](O)=O)=[CH:12]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:45]([NH:52][C:53]1[C:58]([NH2:59])=[CH:57][CH:56]=[C:55]([N:60]2[CH2:65][CH2:64][N:63]([CH3:66])[CH2:62][CH2:61]2)[N:54]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>CN(C=O)C>[CH2:45]([N:52]1[C:53]2=[N:54][C:55]([N:60]3[CH2:61][CH2:62][N:63]([CH3:66])[CH2:64][CH2:65]3)=[CH:56][CH:57]=[C:58]2[N:59]=[C:18]1[C:13]1[CH:14]=[CH:15][C:16](=[O:17])[N:11]([CH3:10])[CH:12]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 592704N(1)-methyl-2-pyridone-5-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117892005N2-benzyl-6-(4-methylpiperazin-1-yl)pyridine-2,3-diamine

Produkt 1

HCID 117889570US9296748, III-1

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (51 mg; 0.392 mmol) is added to a suspension of 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid D-7 (20 mg; 0.131 mmol) and HATU (70 mg; 0.183 mg) in DMF. The mixture is stirred at RT for 5 min. N2-Benzyl-6-(4-methyl-piperazin-1-yl)-pyridine-2,3-diamine E-3.1 is then added and the reaction mixture stirred at RT for 1 h. The reaction mixture is extracted with DCM and NaHCO3 solution. The organic layer is dried over Na2SO4 and concentrated in vacuum. To the formed amide is added 1 ml glacial acetic acid, the reaction is stirred at 120° C. for 2 days. The crude reaction mixture is purified by using reversed phase chromatography (Method: prep. HPLC1).

Aufarbeitung

  1. stirringthe reaction mixture stirred at RT for 1 h
  2. extractionThe reaction mixture is extracted with DCM and NaHCO3 solution
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated in vacuum
  5. additionTo the formed amide is added 1 ml glacial acetic acid
  6. stirringthe reaction is stirred at 120° C. for 2 days
  7. customThe crude reaction mixture
  8. customis purified

Quellen und Nachweise

ORD-Eintrag
ord-3db050a642db4dc68a791dd85db22df9
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296748B2

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