Quinoline-4-carbonyl chloride hydrochloride → 1-cyclopentyl-3-ethyl-4-cyano-5-(4-quinolinecarboxamido)-1H-pyrazole

HRID 1736548Notes

Reaction equation

HRID 1736548 reaction equation
Cl.[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12](Cl)=[O:13])=[CH:4][CH:3]=1.[CH:15]1([N:20]2[C:24]([NH2:25])=[C:23]([C:26]#[N:27])[C:22]([CH2:28][CH3:29])=[N:21]2)[CH2:19][CH2:18][CH2:17][CH2:16]1>>[CH:15]1([N:20]2[C:24]([NH:25][C:12]([C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[N:2]=[CH:3][CH:4]=3)=[O:13])=[C:23]([C:26]#[N:27])[C:22]([CH2:28][CH3:29])=[N:21]2)[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 12373997Quinoline-4-carbonyl chloride hydrochlorideHCID 158712691-cyclopentyl-3-ethyl-4-cyano-5-amino-1H-pyrazole

Product 1

HCID 194328031-cyclopentyl-3-ethyl-4-cyano-5-(4-quinolinecarboxamido)-1H-pyrazoleYield 101.5%

Conditions

Temperature
250 °C

Procedure

4-Quinolinecarboxylic acid chloride hydrochloride (3.8 g, 16.5 mmol) and 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carbonitrile (2.8 g, 13.7 mmol) were combined and heated in an oil bath at 250° C. for 7 minutes. The reaction mixture was cooled to room temperature and the obtained solid was collected by filtration on a glass frit and was washed with chloroform. The residue was recrystallized from ethyl acetate to afford 5.0 g (100%) of 1-cyclopentyl-3-ethyl-4-cyano-5-(4-quinoline-carboxamido)-1H-pyrazole as a white solid, m.p. 156°-161° C., after drying at 110° C. for 7 hours in high vacuum.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe obtained solid was collected by filtration on a glass frit
  3. washwas washed with chloroform
  4. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a517bda8c3c54b51ace9a53312ebac86
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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