Acetic Acid → HCID 68953978, compound

HRID 1453832Notes

Reaction equation

HRID 1453832 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:22]([O:24][CH3:25])=[O:23])=[N:11][N:12]([CH2:18][C:19](=O)[CH3:20])[C:13]=1[C:14](OC)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][NH2:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:10]([C:22]([O:24][CH3:25])=[O:23])=[N:11][N:12]2[CH2:18][CH:19]([CH3:20])[N:27]([CH3:26])[C:14](=[O:15])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 68954281Dimethyl 4-benzyloxy-1-(2-oxopropyl)-1H-pyrazole-3,5-dicarboxylate

Product 1

HCID 68953978HCID 68953978, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of dimethyl 4-benzyloxy-1-(2-oxopropyl)-1H-pyrazole-3,5-dicarboxylate (80 mg, 0.231 mmol) in anhydrous CH2Cl2 were added methylamine (173 μL, 2.0M in THF), sodium triacetoxyborohydride (98 mg, 0.462 mmol), and AcOH (20 μL, 0.346 mmol). The reaction was stirred at room temperature overnight. Toluene was added to replace the evaporated solvent, and the mixture was heated to 110° C. for 3 h. The solvent was removed in vacuo, and purification was achieved by reverse phase chromatography on a C-18 column using a gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA). Collection and concentration of the appropriate fractions afforded the title product as a yellow oil. ES MS (M+1)=330.

Workup

  1. temperaturethe mixture was heated to 110° C. for 3 h
  2. customThe solvent was removed in vacuo, and purification
  3. washa gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA)
  4. customCollection and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-14250e6340dc41109fe5ea243a6a8611
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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