Pyridine → 1-cyclopentyl-3-phenylmethyl-4-cyano-5-(phenylmethylcarbonylamino)-1H-pyrazole

HRID 2257015Notes

Reaction equation

HRID 2257015 reaction equation
[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]#[N:13])[C:8]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[C:27]1([CH2:33][C:34](Cl)=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)(Cl)Cl>[CH:1]1([N:6]2[C:10]([NH:11][C:34]([CH2:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:35])=[C:9]([C:12]#[N:13])[C:8]([CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7679Phenylacetyl chlorideHCID 218309241-cyclopentyl-3-phenylmethyl-4-cyano-5-amino-1H-pyrazole

Product 1

HCID 218308801-cyclopentyl-3-phenylmethyl-4-cyano-5-(phenylmethylcarbonylamino)-1H-pyrazoleYield 88%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 1-cyclopentyl-3-phenylmethyl-5-amino-1H-pyrazole-4-carbonitrile (2.3 g, 8.6 mmol), CHCl3 (50 ml) and pyridine (20 ml) in an ice bath was added a solution of phenylacetyl chloride (2.3 ml, 17.2 mmol) in CHCl3 (10 ml) over a period of 20 minutes. The reaction mixture was stirred in an ice bath for 3 hours, then at room temperature for 2 hours. The solvent was removed in vacuo, the residue was partitioned between CHCl3 (100 ml) and water (50 ml), and the organic layer was separated. Concentration of the organic layer afforded a gummy solid which was recrystallized from isopropanol to afford 1.1 g (88%) of 1-cyclopentyl-3-phenylmethyl-4-cyano-5-(phenylmethylcarbonylamino)-1H-pyrazole, as white needles, m.p. 166°-168° C.

Workup

  1. waitat room temperature for 2 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between CHCl3 (100 ml) and water (50 ml)
  4. customthe organic layer was separated
  5. customConcentration of the organic layer afforded a gummy solid which
  6. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-cba4de7ca2eb4457a3ee55575a894b08
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

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