Sodium Hydroxide → 1-methyl-4-(trityl-amino)-1H-pyrazole-3-carboxylic acid

HRID 720687Notes

Reaction equation

HRID 720687 reaction equation
C[O:2][C:3]([C:5]1[C:9]([NH:10][C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][N:7]([CH3:30])[N:6]=1)=[O:4].[OH-].[Na+]>CO>[CH3:30][N:7]1[CH:8]=[C:9]([NH:10][C:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:5]([C:3]([OH:4])=[O:2])=[N:6]1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 587392481-methyl-4-(trityl-amino)-1H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 218918281-methyl-4-(trityl-amino)-1H-pyrazole-3-carboxylic acidYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 1-methyl-4-(trityl-amino)-1H-pyrazole-3-carboxylic acid methyl ester (70 mg, 0.18 mmol) in methanol (2.0 mL) cooled to 0° C. was treated with a 1N aqueous sodium hydroxide solution (0.7 mL, 0.70 mmol). The reaction was stirred at 25° C. for 18 h. At this time, the reaction was treated with another portion of a 1N aqueous sodium hydroxide solution (0.7 mL, 0.70 mmol). The reaction was stirred for 24 h. At this time, the reaction was warmed to 50° C. for 5 days. At this time, the reaction was concentrated in vacuo. The residue was dissolved into dichloromethane and methanol and then brought to pH=4 by the addition of a 1N aqueous hydrochloric acid solution. The resulting mixture was concentrated in vacuo. The solids were slurried in cold water, collected by filtration, washed with water, and dried in vacuo to afford 1-methyl-4-(trityl-amino)-1H-pyrazole-3-carboxylic acid (60 mg, 88.9%) as an off-white solid: EI-HRMS m/e calcd for C24H21N3O2 (M+Na)+ 406.1526, found 406.1526.

Workup

  1. stirringThe reaction was stirred for 24 h
  2. temperatureAt this time, the reaction was warmed to 50° C. for 5 days
  3. concentrationAt this time, the reaction was concentrated in vacuo
  4. dissolutionThe residue was dissolved into dichloromethane and methanol
  5. additionbrought to pH=4 by the addition of a 1N aqueous hydrochloric acid solution
  6. concentrationThe resulting mixture was concentrated in vacuo
  7. filtrationcollected by filtration
  8. washwashed with water
  9. customdried in vacuo

Sources & evidence

ORD record
ord-63d5e8ff7333465ea130ca21a9950239
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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