p-Toluenesulfonic acid → HCID 178437858, compound

HRID 619161Notes

Reaction equation

HRID 619161 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.[N:17]1([CH2:23][CH2:24][O:25][C:26]2[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=2)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH:1]1([N:6]2[C:10]3=[N:11][C:30]([C:29]4[CH:32]=[CH:33][C:26]([O:25][CH2:24][CH2:23][N:17]5[CH2:22][CH2:21][O:20][CH2:19][CH2:18]5)=[CH:27][CH:28]=4)=[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

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 37199024-(2-Morpholinoethoxy)benzaldehydeHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437858HCID 178437858, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.19 g, 9.86 mmol), 4-[2-(4-morpholinyl)ethoxy]benzaldehyde (3.5 g) and xylenes (10 ml) was heated at 160° C. overnight. p-Toluenesulfonic acid (0.2 g) was added and the mixture was heated at 160° C. overnight. The reaction mixture was cooled to room temperature, and the precipitate which formed was slurried with methanol, collected by filtration and washed with methanol, and then ether. The product was recrystallized from acetonitrile to afford 1-cyclopentyl-3-ethyl-6-[4-[2-(4-morpholinyl)ethoxy]phenyl]pyrazolo[3,4-d]pyrimidin-4-one.

Workup

  1. temperaturethe mixture was heated at 160° C. overnight
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe precipitate which formed
  4. filtrationcollected by filtration
  5. washwashed with methanol
  6. customThe product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-7b1b651fc8ac4a62a284f9f3ad6022e3
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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