p-Toluenesulfonic acid → HCID 178437839, compound

HRID 1597836Notes

Reaction equation

HRID 1597836 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][O:18][C:19]1[CH:20]=[CH:21][C:22](C=O)=[CH:23][CH:24]=1.[C:27]1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:27]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[O:18][CH3:17])=[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 312444-MethoxybenzaldehydeHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437839HCID 178437839, compoundYield 127.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.0 g, 9 mmol), anisaldehyde (2.45 g, 18 mmol), xylenes (50 ml) and p-toluenesulfonic acid (0.5 g) was refluxed for 32 hours. The reaction mixture was stripped to dryness, treated with ethanol (100 ml) and then again concentrated to dryness. The residue was treated with CHCl3 (100 ml) and 10% K2CO3 (100 ml), the layers were separated and the aqueous layer was extracted with chloroform (3×100 ml). The combined organic layers were concentrated to approximately 25 ml and then combined with silica gel (30 g). The preloaded silica was placed on a silica gel column and eluted with ether/hexanes (8/10) to ether (100%) to afford 1.25 g (41%) of 1-cyclopentyl-3-ethyl-6-(2-methoxyphenyl)-pyrazolo[3,4-d]pyrimidin-4-one, m.p. 135°-136° C., after recrystallization from cyclohexane.

Workup

  1. temperaturewas refluxed for 32 hours
  2. concentrationagain concentrated to dryness
  3. additionThe residue was treated with CHCl3 (100 ml) and 10% K2CO3 (100 ml)
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with chloroform (3×100 ml)
  6. concentrationThe combined organic layers were concentrated to approximately 25 ml
  7. washeluted with ether/hexanes (8/10) to ether (100%)

Sources & evidence

ORD record
ord-14a488a0ca6d4a65b84ba76119c68e29
Source dataset
uspto-grants-1998_04
Patent number
US05736548

Reaction notes

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