Isonicotinoyl chloride hydrochloride → 1-cyclopentyl-3-phenylmethyl-4-cyano-5-(4-pyridinecarboxamido)-1H-pyrazole

HRID 1736556Notes

Reaction equation

HRID 1736556 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([C:8](Cl)=[O:9])=[CH:4][CH:3]=1.[CH:11]1([N:16]2[C:20]([NH2:21])=[C:19]([C:22]#[N:23])[C:18]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:17]2)[CH2:15][CH2:14][CH2:13][CH2:12]1>>[CH:11]1([N:16]2[C:20]([NH:21][C:8]([C:5]3[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=3)=[O:9])=[C:19]([C:22]#[N:23])[C:18]([CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[N:17]2)[CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

3

Reactant 2

HCID 12262826Isonicotinoyl chloride hydrochlorideHCID 218309241-cyclopentyl-3-phenylmethyl-4-cyano-5-amino-1H-pyrazole

Product 1

HCID 194327571-cyclopentyl-3-phenylmethyl-4-cyano-5-(4-pyridinecarboxamido)-1H-pyrazoleYield 85.3%

Conditions

Temperature
200 °C

Procedure

4-Pyridinecarboxylic acid chloride hydrochloride (4.3 g, 24 mmol), and 1-cyclopentyl-3-phenylmethyl-4-cyano-5-amino-1H-pyrazole (3.2 g, 12.0 mmol) were combined and heated to 200° C. under argon for 5 minutes. The reaction mixture was cooled to room temperature and the residue was partitioned between chloroform and sat. NaHCO3. The organic layer was separated, washed with additional sat. NaHCO3, dried over anhydrous MgSO4 passed through a plug of silica and the solvent was removed in vacuo to afford 3.8 g (84%) of 1-cyclopentyl-3-phenylmethyl-4-cyano-5-(4-pyridinecarboxamido)-1H-pyrazole as white crystals, m.p. 189°-191° C. when recrystallized from ethyl acetate and dried at 80° C. for 8 hours in high vacuum.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe residue was partitioned between chloroform and sat. NaHCO3
  3. customThe organic layer was separated
  4. washwashed with additional sat. NaHCO3
  5. dry with materialdried over anhydrous MgSO4
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-060327727fcf4afb8a69da5461adf655
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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