Water → HCID 178437880, compound

HRID 1600795Notes

Reaction equation

HRID 1600795 reaction equation
[Na].[CH:2]1([N:7]2[C:11]([NH2:12])=[C:10]([C:13]([NH2:15])=[O:14])[C:9]([CH2:16][CH3:17])=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[N:18]1([CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][C:34](OC)=O)=[CH:29][CH:28]=2)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.O>C(O)C.CCOCC.C(O)(=O)C>[CH:2]1([N:7]2[C:11]3=[N:12][C:34]([CH2:33][C:30]4[CH:31]=[CH:32][C:27]([O:26][CH2:25][CH2:24][N:18]5[CH2:23][CH2:22][O:21][CH2:20][CH2:19]5)=[CH:28][CH:29]=4)=[N:15][C:13](=[O:14])[C:10]3=[C:9]([CH2:16][CH3:17])[NH:8]2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 962WaterHCID 5360545SodiumHCID 21830903Methyl 4-[2-(4-morpholinyl)ethoxy]phenylacetateHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437880HCID 178437880, compoundYield 41.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Sodium (414 mg) was dissolved in ethanol (30 ml) and 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.0 g) and methyl 4-[2-(4-morpholinyl)ethoxy]phenylacetate (5.03 g, 18 mmol) were added. The reaction mixture was refluxed overnight, the solvent was stripped, water was added to the residue, followed by sufficient acetic acid to adjust the pH to 8-9. An oil separated which was collected by decantation and treated with water and saturated NaHCO3. The mixture was extracted with ethyl acetate and washed with water and then saturated NaHCO3 (2×). The aqueous layer was extracted with additional ethyl acetate and the combined organic layers were washed with 2N NaOH and brine. The organic layer was dried over MgSO4, filtered and stripped to afford crude product which was digested with ether and collected by filtration. The crude product was purified by several acid/base work-ups, followed by recrystallization from ether to afford 1.67 g of 1-cyclopentyl-3-ethyl-6-[4-[2-(4-morpholinyl)ethoxy]phenylmethyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 136-137° C.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customAn oil separated which
  3. customwas collected by decantation
  4. additiontreated with water and saturated NaHCO3
  5. extractionThe mixture was extracted with ethyl acetate
  6. washwashed with water
  7. extractionThe aqueous layer was extracted with additional ethyl acetate
  8. washthe combined organic layers were washed with 2N NaOH and brine
  9. dry with materialThe organic layer was dried over MgSO4
  10. filtrationfiltered
  11. customto afford crude product which
  12. filtrationcollected by filtration
  13. customThe crude product was purified by several acid/base work-ups
  14. customfollowed by recrystallization from ether

Sources & evidence

ORD record
ord-3d49753fd5744dc98b82fe5877d3cf97
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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