Hydrochloric Acid → HCID 59587421, compound

HRID 1410425Notes

Reaction equation

HRID 1410425 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[NH:12][C:13]=2[C:14]([O:16]CC)=[O:15])=[CH:5][CH:4]=1.N1C=CC(C=O)=CC=1.[OH-].[K+].Cl>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]([C:19]3[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=3)[NH:12][C:13]=2[C:14]([OH:16])=[O:15])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 133894-PyridinecarboxaldehydeHCID 14797Potassium HydroxideHCID 68521887HCID 68521887, compound

Product 1

HCID 59587421HCID 59587421, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of ethyl 4-(4-methoxyphenyl)-2-(pyridin-4-yl)-1H-imidazole-5-carboxylate (0.089 g, 0.28 mmol, prepared (using pyridine-4-carboxaldehyde in place of benzaldehyde) according to the method outlined in Example A-1, step c), in methanol was added 1M aqueous potassium hydroxide (5 m, 5.0 mmol) and the resulting mixture stirred at 55° C. for 48 hours. The solution was cooled to room temperature, neutralised by the addition of 0.5M aqueous HCl and extracted with DCM. The aqueous phase was then acidified by the addition of acetic acid and purified by SPE using MP-TsOH cartridges (2×1000 mg) to afford 4-(4-methoxyphenyl)-2-(pyridin-4-yl)-1H-imidazole-5-carboxylic acid (0.090 g) as an orange oil which was used without further purification. LCMS (2) Rt: 1.20 min; m/z (ES+) 296.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionextracted with DCM
  3. additionThe aqueous phase was then acidified by the addition of acetic acid
  4. custompurified by SPE

Sources & evidence

ORD record
ord-72601ed6fa034583a8adaa152c85f761
Source dataset
uspto-grants-2014_12
Patent number
US08921544B2

Reaction notes

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