o-(Trifluoromethyl)benzaldehyde → HCID 178437835, compound

HRID 619155Notes

Reaction equation

HRID 619155 reaction equation
[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([NH2:14])=[O:13])[C:8]([CH2:15][CH3:16])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:17][C:18]([F:28])([F:27])[C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=O>C(O)(=O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:21]([C:20]4[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=4[C:18]([F:17])([F:27])[F:28])=[N:14][C:12](=[O:13])[C:9]3=[C:8]([CH2:15][CH3:16])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 123067o-(Trifluoromethyl)benzaldehydeHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437835HCID 178437835, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (0.59 g, 2.65 mmol), 2-trifluoromethylbenzaldehyde (0.5 ml) and glacial acetic acid (25 ml) was refluxed overnight and then 0.5 equivalents of additional aldehyde was added and the mixture was refluxed for about 3 days. The reaction mixture was cooled to room temperature, the acetic acid was stripped and the residue was cooled and rinsed with ether to give a white solid which was collected by filtration and recrystallized from tert-butyl dimethyl ether/hexanes to afford 1-cyclopentyl-3-ethyl-6-(2-trifluoromethylphenyl)-pyrazolo[3,4-d]pyrimidin-4-one, m.p. 201-202° C.

Workup

  1. temperaturewas refluxed overnight
  2. temperaturethe mixture was refluxed for about 3 days
  3. temperaturethe residue was cooled
  4. washrinsed with ether
  5. customto give a white solid which
  6. filtrationwas collected by filtration
  7. customrecrystallized from tert-butyl dimethyl ether/hexanes

Sources & evidence

ORD record
ord-8739e9be9a1c43e3be9877a1157c1e08
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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