Ammonia → HCID 67027581, compound

HRID 2400360Notes

Reaction equation

HRID 2400360 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([C:10]([NH:12][NH2:13])=O)=[CH:6][C:5]=12.[CH3:14][C:15]([CH:17]=O)=O.[NH3:19]>C(O)C>[CH3:14][C:15]1[N:19]=[C:10]([C:7]2[CH:8]=[CH:9][N:4]3[CH:3]=[CH:2][N:1]=[C:5]3[CH:6]=2)[N:12]=[N:13][CH:17]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 880MethylglyoxalHCID 55281632Imidazo[1,2-a]pyridine-7-carbohydrazide

Product 1

HCID 67027581HCID 67027581, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of imidazo[1,2-a]pyridine-7-carboxylic acid hydrazide (705 mg, 4.0 mmol, 1.0 equiv) and pyruvic aldehyde (40 wt % in water, 0.8 ml) in ethanol (10 ml) was stirred at room temperature for 2.5 hours. Ammonia (2M in methanol, 10 ml) was added and stirred at room temperature for 15 minutes before heating to 100 deg C. in a microwave for 60 minutes. The reaction mixture was concentrated in vacuo and dichloromethane was added. After stirring at room temperature for 15 minutes the solid (recovered starting material) was filtered off and the liquors were purified by column chromatography (0-10% methanol/dichloromethane) furnishing 200 mg of a yellow solid. MS: [M+H]+212

Workup

  1. stirringstirred at room temperature for 15 minutes
  2. temperaturebefore heating to 100 deg C
  3. waitin a microwave for 60 minutes
  4. concentrationThe reaction mixture was concentrated in vacuo and dichloromethane
  5. additionwas added
  6. stirringAfter stirring at room temperature for 15 minutes
  7. customthe solid (recovered starting material)
  8. filtrationwas filtered off
  9. customthe liquors were purified by column chromatography (0-10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-55f02ad8d5b8411f8dfede7065b1320b
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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