2-Chloroaniline → HCID 24771611, Verbindung

HRID 645363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 645363
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.ONN1C=CN=N1.C(N(CC)C(C)C)(C)C.[Cl:49][C:50]1[CH:51]=[CH:52][C:53]2[N:54]([CH:56]=[C:57]([C:59](O)=[O:60])[N:58]=2)[CH:55]=1>CN(C)C=O.C(=O)([O-])O.[Na+]>[Cl:49][C:50]1[CH:51]=[CH:52][C:53]2[N:54]([CH:56]=[C:57]([C:59]([NH:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[Cl:1])=[O:60])[N:58]=2)[CH:55]=1

Komponenten

8

Edukt 5

HCID 72402-ChloroanilineHCID 81531DiisopropylethylamineHCID 27576146-chloroimidazo[1,2-a]pyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 136346319HCID 136346319, Verbindung

Produkt 1

HCID 24771611HCID 24771611, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

54 μl of 2-chloroaniline, 211 mg of HATU, 75 mg of 1-hydroxyaminotriazole and 237 μl of N,N-diisopropylethylamine are added to a solution of 100 mg of 6-chloroimidazo[1,2-a]pyridine-2-carboxylic acid in 1 ml of N,N-dimethylformamide. The reaction mixture is heated at 70° C. for 16 hours, diluted with a saturated sodium hydrogencarbonate solution and extracted with ethyl acetate. The combined organic phases are dried and concentrated under reduced pressure. The residue is purified by flash chromatography on silica, elution being carried out with a hexane/ethyl acetate 70/30 mixture to give 62 mg of 6-chloro-N-(2-chlorophenyl)imidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. customThe combined organic phases are dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by flash chromatography on silica, elution

Quellen und Nachweise

ORD-Eintrag
ord-e642ba07940644169aad1ad2344d58f2
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07704989B2

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