Formic Acid → HCID 178469440, compound

HRID 2363750Notes

Reaction equation

HRID 2363750 reaction equation
[NH:1]([C:3](=[NH:18])[C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=2)[CH:9]=1)[NH2:2].[CH:19](O)=O>>[NH:2]1[CH:19]=[N:18][C:3]([C:4]2[CH:5]=[CH:6][C:7]3[N:8]([CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=3)[CH:9]=2)=[N:1]1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 178469445HCID 178469445, compound

Product 1

HCID 178469440HCID 178469440, compound

Conditions

Temperature
85 °C

Procedure

A suspension of 580 mg of ethyl 6-[hydrazino(imino)methyl]imidazo[1,2-a]pyridine-2-carboxylate in 6 mL of formic acid is heated for 20 hours at 85° C. The reaction mixture is concentrated to less than 20% of its initial volume and diluted with 20 mL of water. Solid sodium carbonate is added at 0-5° C. to obtain a pH of 8-9. The precipitate is filtered off by suction, and then purified by chromatography on silica, eluting with a mixture of dichloromethane and methanol (98/2) to give 320 mg of ethyl 6-(1H-1,2,4-triazol-3-yl)imidazo[1,2-a]pyridine-2-carboxylate.

Workup

  1. concentrationThe reaction mixture is concentrated to less than 20% of its initial volume
  2. additiondiluted with 20 mL of water
  3. additionSolid sodium carbonate is added at 0-5° C.
  4. customto obtain a pH of 8-9
  5. filtrationThe precipitate is filtered off by suction
  6. custompurified by chromatography on silica
  7. washeluting with a mixture of dichloromethane and methanol (98/2)

Sources & evidence

ORD record
ord-f9a73176561c4b3d9fe3e159e711fc3b
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

Loading…