Ammonia → 3-(4-aminophenyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

HRID 550890

Reaktionsgleichung

Reaktionsgleichung von HRID 550890
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([O:19]CC)=O)=[CH:4][CH:3]=1.[NH3:22].C>CO>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([NH2:22])=[O:19])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 222Ammonia2×HCID 297MethaneHCID 57445352ethyl 3-(4-aminophenyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Produkt 1

HCID 574453513-(4-aminophenyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 600 mg of ethyl 3-(4-aminophenyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate in 62 mL of a 3N solution of ammonia in methanol are added 11 mL of 22% aqueous ammonia solution. The reaction mixture is stirred for 20 hours in an autoclave at 80° C. (12 bar) and then concentrated under reduced pressure. The residue obtained is diluted in 100 mL of methanol, treated with carbon black and refluxed for 30 minutes. The mixture is filtered while hot through Celite and then rinsed with 2×10 mL of methanol. The filtrate is concentrated under reduced pressure to give 490 mg of 3-(4-aminophenyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide in the form of a foam, the characteristics of which are as follows:

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. temperaturerefluxed for 30 minutes
  4. filtrationThe mixture is filtered while hot through Celite
  5. washrinsed with 2×10 mL of methanol
  6. concentrationThe filtrate is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c60b686cf9d64fde9506cbd257302c6d
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947706B2

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