Hydrochloric Acid → 1-Methyl-5-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)ethylcarbamoyl)-1H-pyrazole-4-carboxylic acid

HRID 1621141Notes

Reaction equation

HRID 1621141 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[O:21])[NH:8][CH2:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[N:12]=2)=[C:5]([C:22]([O:24]CC)=[O:23])[CH:4]=[N:3]1.[Li+].[OH-].Cl>C1COCC1.C(O)C>[CH3:1][N:2]1[C:6]([C:7](=[O:21])[NH:8][CH2:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[N:12]=2)=[C:5]([C:22]([OH:24])=[O:23])[CH:4]=[N:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71279145Ethyl 1-methyl-5-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)ethylcarbamoyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 712791711-Methyl-5-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)ethylcarbamoyl)-1H-pyrazole-4-carboxylic acidYield 74.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-methyl-5-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)ethylcarbamoyl)-1H-pyrazole-4-carboxylate (76 mg, 214 μmol) in THF (0.9 mL) and ethanol (0.3 mL) was added LiOH (1M aqueous solution, 428 μL, 428 μmol) at 0-5° C. The mixture was stirred at RT for 2 h. HCl (1M aqueous solution, 0.43 mL, 0.43 mmol) was added and the precipitating product was filtered, washed with THF/water 4:1 and dried in vacuo to give the product as colorless solid (52 mg, 159 μmol, 74.3%).

Workup

  1. filtrationthe precipitating product was filtered
  2. washwashed with THF/water 4:1
  3. customdried in vacuo

Sources & evidence

ORD record
ord-5784a965518f411b9835b13f9903818f
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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