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

HRID 405810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405810
[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-88da2bd1aa744843aafbbffa16b1b2b5
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754071B2

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