p-Toluenesulfonic acid → HCID 178437857, compound

HRID 619148Notes

Reaction equation

HRID 619148 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.[CH3:17][N:18]([CH3:31])[CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH:1]1([N:6]2[C:10]3=[N:11][C:27]([C:26]4[CH:25]=[CH:24][C:23]([O:22][CH2:21][CH2:20][CH2:19][N:18]([CH3:31])[CH3:17])=[CH:30][CH:29]=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

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 5469324-[3-(Dimethylamino)propoxy]benzaldehydeHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437857HCID 178437857, compound

Conditions

Temperature
120 °C

Procedure

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.03 g, 9.14 mmol), 4-[3-(dimethylamino)propoxy]benzaldehyde (2.76 ml), and xylenes was heated at 120° C. for 1 hour, then at 160° C. for 6 hours. p-Toluenesulfonic acid (300 mg) was added and the mixture was heated at 160° C. until the reaction was complete. The reaction mixture was cooled to room temperature, and a creamy white solid formed, which was collected by filtration, washed with methanol and recrystallized from ethyl acetate to afford 1-cyclopentyl-3-ethyl-6-[4-[3-(dimethylamino)propoxy]phenyl]pyrazolo[3,4-d]pyrimidin-4-one, as a white solid, m.p. 175-178° C.

Workup

  1. temperaturethe mixture was heated at 160° C. until the reaction
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customa creamy white solid formed
  4. filtrationwhich was collected by filtration
  5. washwashed with methanol
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-27ee8929207943359e188d7c8ec80ded
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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