Hydrochloric Acid → 2-methyl-4-[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]-1H-imidazol-1-amine

HRID 1907178Notes

Reaction equation

HRID 1907178 reaction equation
Cl.[CH3:2][C:3]1[N:4]([NH:21]C(=O)C)[CH:5]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH3:20])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:7]=1.[OH-].[Na+]>CO>[CH3:2][C:3]1[N:4]([NH2:21])[CH:5]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH3:20])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 68181857N-{2-methyl-4-[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]-1H-imidazol-1-yl}acetamide

Product 1

HCID 681818812-methyl-4-[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]-1H-imidazol-1-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous hydrochloric acid (1 N, 7.0 mL) was added to a solution of N-{2-methyl-4-[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]-1H-imidazol-1-yl}acetamide (236 mg, 0.763 mmol) in methanol (1.0 mL), and the mixture was heated at reflux for 30 minutes. Additional 1 N aqueous hydrochloric acid (2.0 mL) was added, and heating was continued for an additional 30 minutes. After cooling, the solution was basified with 1 N aqueous sodium hydroxide solution, and the mixture was extracted twice with ethyl acetate containing 1% methanol. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the product as a yellow solid. Yield: 148.5 mg, 0.5555 mmol, 73%. LCMS m/z 268.5 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.39 (s, 3H), 2.45 (br s, 3H), 3.70 (s, 3H), 4.45 (br s, 2H), 6.26 (s, 1H), 7.24-7.32 (m, 4H, assumed; partially obscured by solvent peak), 7.97 (s, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. temperatureheating
  4. temperatureAfter cooling
  5. extractionthe mixture was extracted twice with ethyl acetate containing 1% methanol
  6. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6eedcffe37948e296e6ec63f7e9f159
Source dataset
uspto-grants-2013_12
Patent number
US08598155B2

Reaction notes

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