Hydrochloric Acid → HCID 178485487, compound

HRID 130669Notes

Reaction equation

HRID 130669 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:13]([NH:15][CH3:16])=[O:14])=[C:10]([CH3:12])[N:11]=[C:5]2[CH:4]=1.[Na].Cl.CO>CN(C=O)C>[OH:2][C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:13]([NH:15][CH3:16])=[O:14])=[C:10]([CH3:12])[N:11]=[C:5]2[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 5360545SodiumHCID 860551557-methoxy-N,2-dimethylimidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 178485487HCID 178485487, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 7-methoxy-N,2-dimethylimidazo[1,2-α]pyridine-3-carboxamide (985 mg, 4.49 mmol) in DMF (20 ml) was added sodium thioethylate (80% pure, 1.86 g, 18 mmol) and the mixture heated to 120° C. for 2 hours. After cooling to ambient temperature, the reaction was neutralized to pH 6 with 1N HCl and concentrated in vacuo. The residue was dissolved in MeOH/H2O, pre-absorbed onto SiO2, and purified by flash chromatography (eluting with 90/10/1-80/20/5, DCM/MeOH/cNH3) to yield the crude product as a yellow solid, which was titrated with MeOH to yield 7-hydroxy-N,2-dimethylimidazo[1,2-α]pyridine-3-carboxamide 111-B, 700 mg, 78%, as a pale yellow solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in MeOH/H2O
  4. custompre-absorbed onto SiO2
  5. custompurified by flash chromatography (eluting with 90/10/1-80/20/5, DCM/MeOH/cNH3)
  6. customto yield the crude product as a yellow solid, which

Sources & evidence

ORD record
ord-d317814f0b3d48c59899c70c3eb44e86
Source dataset
uspto-grants-2008_06
Patent number
US07381824B2

Reaction notes

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