1-methyl-1H-pyrazol-4-amine → HCID 178481770, compound

HRID 2119665Notes

Reaction equation

HRID 2119665 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH2:7])[CH:4]=[N:3]1.O=[C:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[C:15]([O-])=[O:16]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][N:2]1[C:6]2[C:5](=[N:7][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:15]=2[OH:16])[CH:4]=[N:3]1

Participants

5

Reactant 2

HCID 47709901-methyl-1H-pyrazol-4-amineHCID 21959055HCID 21959055, compound

Product 1

HCID 178481770HCID 178481770, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A solution of 1-methyl-1H-pyrazol-4-amine ((J. Catalan et al., J. Heterocycl. Chem., 1985, 22, 997), 200 mg, 2.06 mmol), 2-oxocyclohexanecarboxylate (351 mg, 2.06 mmol), and p-toluenesulfonic acid monohydrate (10 mg, 0.05 mmol) in toluene (20 ml) was stirred at 120° C. for 2.5 h. After cooling to room temperature, the solvent was removed in vacuo. Diphenyl ether (5 ml) was added to the residue (ca. 300 mg) and the resulting mixture was heated at 240° C. for 40 min. After cooling to room temperature, hexane (2 ml) was added. The precipitate was collected by filtration and washed with dichloromethane to give 190 mg (46%) of the title compound as a white solid.

Workup

  1. customthe solvent was removed in vacuo
  2. additionDiphenyl ether (5 ml) was added to the residue (ca. 300 mg)
  3. temperaturethe resulting mixture was heated at 240° C. for 40 min
  4. temperatureAfter cooling to room temperature
  5. additionhexane (2 ml) was added
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with dichloromethane

Sources & evidence

ORD record
ord-2a889fbc4de945e98e283b924c1682de
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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