3-(2-Morpholin-4-ylethoxy)benzaldehyde → HCID 178437845, compound

HRID 619154Notes

Reaction equation

HRID 619154 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:27]=[C:28]([CH:31]=[CH:32][CH:33]=2)[CH:29]=O)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>>[CH:1]1([N:6]2[C:10]3=[N:11][C:29]([C:28]4[CH:31]=[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]=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

3

Reactant 2

HCID 71646203-(2-Morpholin-4-ylethoxy)benzaldehydeHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437845HCID 178437845, compound

Conditions

Temperature
160 °C

Procedure

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (1.05 g, 4.73 mmol), 3-[2-(4-morpholinyl)ethoxy]benzaldehyde (1.67 g) and xylenes (7 ml) was heated to 160° C. overnight. Additional aldehyde (0.4 g) 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 solid formed which was collected by filtration and washed with ether. The filtrate was concentrated to dryness and the residue was combined with the solid and was purified by column chromatography on silica gel eluting with ethyl acetate/ethanol (60/40). The solid product thus obtained was washed with ether, recrystallized from ethyl acetate and then washed with ether again to afford 1-cyclopentyl-3-ethyl-6-[3-[2-(4-morpholinyl)ethoxy]phenyl]-pyrazolo[3,4-d]pyrimidin-4-one, m.p. 173-176° C.

Workup

  1. temperaturethe mixture was heated at 160° C. until the reaction
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customa solid formed which
  4. filtrationwas collected by filtration
  5. washwashed with ether
  6. concentrationThe filtrate was concentrated to dryness
  7. customwas purified by column chromatography on silica gel eluting with ethyl acetate/ethanol (60/40)
  8. customThe solid product thus obtained
  9. washwas washed with ether
  10. customrecrystallized from ethyl acetate
  11. washwashed with ether again

Sources & evidence

ORD record
ord-06df213433b4466ab6af85dd9bff86f6
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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