1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(Cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide

HRID 1696224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696224
[CH:1]1([NH:7][C:8]2[C:13]([C:14](O)=[O:15])=[CH:12][N:11]=[C:10]3[NH:17][CH:18]=[CH:19][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[N:21]1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[Cl-].[NH4+]>CN(C)C=O.C(Cl)(Cl)Cl.O>[CH:1]1([NH:7][C:8]2[C:13]([C:14]([NH2:21])=[O:15])=[CH:12][N:11]=[C:10]3[NH:17][CH:18]=[CH:19][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

8

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 672772414-(Cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

Produkt 1

HCID 672781964-(Cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamideAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 4-(cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (5.0 mg) in N,N-dimethylformamide (0.1 mL) were added 1-hydroxybenzotriazole (3.9 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (4.5 mg). The mixture was stirred at 60° C. for 30 minutes. To the solution was added ammonium chloride and the mixture was stirred at ambient temperature for 18 hours. To the solution were added water and chloroform and the mixture was extracted with chloroform. The extract was dried over MgSO4, filtrated and evaporated in vacuo. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give 4-(cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (3 mg) as a white powder.

Aufarbeitung

  1. stirringthe mixture was stirred at ambient temperature for 18 hours
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThe extract was dried over MgSO4
  4. filtrationfiltrated
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-ef513ab71fd34a67ae1855dee4a2c52c
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163767B2

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