Butyric Acid → 5-Butyramido-2-propylimidazo[4,5-b]pyridine

HRID 466688

Reaktionsgleichung

Reaktionsgleichung von HRID 466688
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([NH2:11])[N:3]=1.[C:12]([OH:17])(=O)[CH2:13][CH2:14][CH3:15].C(Cl)Cl>CO.O.[NH4+].[OH-].[Pd]>[C:12]([NH:11][C:4]1[N:3]=[C:2]2[N:1]=[C:4]([CH2:5][CH2:6][CH3:7])[NH:8][C:7]2=[CH:6][CH:5]=1)(=[O:17])[CH2:13][CH2:14][CH3:15]

Komponenten

8

Edukt 3

HCID 264Butyric AcidHCID 6344DichloromethaneHCID 3199982,6-Diamino-3-nitropyridine

Produkt 1

HCID 224073815-Butyramido-2-propylimidazo[4,5-b]pyridineAusbeute 49,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 14923Ammonium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2,6-diamino-3-nitropyridine (878 mg, 5.7 mmol) and Pd-C (10%, 100 mg) in MeOH (100 mL) was stirred under 1 atm. H2 for 16 hours. The mixture (containing the air sensitive triamine) was filtered, evaporated, and to this flask was added polyphosphoric acid (15 mL) and butyric acid (1.05 mL, 11.5 mmol). This mixture was heated to 80° C. for 5 hours, cooled to room temperature, diluted with water and neutralized with concentrated NH4OH. Extractive workup (CH2Cl2) gave 345 mg of 5-(butyramido)-2-propylimidazo[4,5-b]pyridine.

Aufarbeitung

  1. filtrationwas filtered
  2. customevaporated
  3. temperaturecooled to room temperature

Quellen und Nachweise

ORD-Eintrag
ord-456bbe93220848599009a8d9c9554856
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05157026

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