3-(2-Morpholino-2-oxoethoxy)benzaldehyde → HCID 178437847, compound

HRID 619189Notes

Reaction equation

HRID 619189 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([C:23]([CH2:25][O:26][C:27]2[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=2)[CH:30]=O)=[O:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>>[CH:1]1([N:6]2[C:10]3=[N:11][C:30]([C:29]4[CH:32]=[CH:33][CH:34]=[C:27]([O:26][CH2:25][C:23]([N:17]5[CH2:22][CH2:21][O:20][CH2:19][CH2:18]5)=[O:24])[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

3

Reactant 2

HCID 164955713-(2-Morpholino-2-oxoethoxy)benzaldehydeHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437847HCID 178437847, compound

Conditions

Temperature
160 °C

Procedure

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (1.87 g), 3-[4-morpholinylcarbonylmethoxy]benzaldehyde (2.1 g, 8.43 mmol) and xylenes (20 ml) was heated at 160° C. for about 2 days. The solvent was removed, then methanol was added to the residue and the product was collected by filtration. Additional product was obtained from the filtrates and the product fractions were pooled and recrystallized from CH3CN/CHCl3 to afford 1-cyclopentyl-3-ethyl-6-[3-(4-morpholinylcarbonylmethoxy)phenyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 212-213° C.

Workup

  1. customThe solvent was removed
  2. additionmethanol was added to the residue
  3. filtrationthe product was collected by filtration
  4. customAdditional product was obtained from the filtrates
  5. customrecrystallized from CH3CN/CHCl3

Sources & evidence

ORD record
ord-294ca64a56334c18bea5079ae8742a13
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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