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

HRID 570326Notes

Reaction equation

HRID 570326 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4ed9e57a0e9947d1854e2a4f94ee4b30
Source dataset
uspto-grants-2015_05
Patent number
US09023839B2

Reaction notes

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