Dimethyl Sulfoxide → 1-ethyl-7-carboxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 375877Notes

Reaction equation

HRID 375877 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15](Cl)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[C:11]([C:17]([OH:19])=[O:18])[CH:10]=3)[CH3:2].CS(C)=O.[CH:24]1([CH2:30][NH2:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.O>C(O)(=O)C>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:31][CH2:30][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[C:11]([C:17]([OH:19])=[O:18])[CH:10]=3)[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 76688CyclohexanemethylamineHCID 212177041-ethyl-4-chloro-7-carboxy-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 212177061-ethyl-7-carboxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-ethyl-4-chloro-7-carboxy-1H-pyrazolo[3,4-b]quinoline (0.9 g, 3.3 mmol), DMSO (9 ml) and cyclohexanemethyl amine (0.86 ml, 6.6 mmol) was heated at 120°-130° C. for 6 hours. The reaction mixture was poured into water, acidified with acetic acid and the solid which formed was collected by filtration, dissolved in 5% NaOH and extracted with CH2Cl2 (2×50 ml). The aqueous layer was acidified with acetic acid and the solid which formed was collected by filtration and washed with water. The solid was purified by column chromatography on silica gel eluting with 30% methanol/10% acetic acid/60% CH2Cl2 to afford 1-ethyl-7-carboxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as a yellow solid.

Workup

  1. temperaturewas heated at 120°-130° C. for 6 hours
  2. customthe solid which formed
  3. filtrationwas collected by filtration
  4. dissolutiondissolved in 5% NaOH
  5. extractionextracted with CH2Cl2 (2×50 ml)
  6. customthe solid which formed
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customThe solid was purified by column chromatography on silica gel eluting with 30% methanol/10% acetic acid/60% CH2Cl2

Sources & evidence

ORD record
ord-bfa05063c31b45bb80a1fa67617994d7
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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