Cyanogen Bromide → N-(5-cyanamido-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 1497876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497876
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:20])=[C:6]([NH:8][C:9]([C:11]2[N:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]3=[N:13][CH:12]=2)=[O:10])[CH:7]=1.CC([O-])=O.[K+].Br[C:27]#[N:28]>CO>[NH:1]([C:2]1[CH:3]=[CH:4][C:5]([CH3:20])=[C:6]([NH:8][C:9]([C:11]2[N:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]3=[N:13][CH:12]=2)=[O:10])[CH:7]=1)[C:27]#[N:28]

Komponenten

5

Edukt 3

HCID 10476Cyanogen BromideHCID 517044Potassium AcetateHCID 86677450N-(5-amino-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

Produkt 1

HCID 86677452N-(5-cyanamido-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To N-(5-amino-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (67) (4.53 g, 15 mmol) in MeOH (100 mL) was added KOAc (4.41 g, 45 mmol) and the mixture was stirred at room temperature for 5 minutes then cooled to 0° C. before a solution of BrCN (1.62 g, 15 mmol) in MeOH (30 mL) was added dropwise. The resulting mixture was slowly warmed to room temperature and stirred overnight. The solvent was evaporated and to the residue was added water (150 mL). The mixture was stirred at room temperature for 1 hour, filtered and washed with water (2×20 mL), then air dried to give N-(5-cyanamido-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (68) as a white solid.

Aufarbeitung

  1. additionwas added dropwise
  2. temperatureThe resulting mixture was slowly warmed to room temperature
  3. stirringstirred overnight
  4. customThe solvent was evaporated and to the residue
  5. additionwas added water (150 mL)
  6. stirringThe mixture was stirred at room temperature for 1 hour
  7. filtrationfiltered
  8. washwashed with water (2×20 mL)
  9. customair dried

Quellen und Nachweise

ORD-Eintrag
ord-38f6a944d6764e2a9cf34468e33afea9
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199981B2

Notizen zur Reaktion

Wird geladen…