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

HRID 405810ノート

反応式

HRID 405810 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-88da2bd1aa744843aafbbffa16b1b2b5
出典データセット
uspto-grants-2014_06
特許番号
US08754071B2

反応ノート

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