Dimethyl Sulfoxide → HCID 19592223, compound

HRID 1456028Notes

Reaction equation

HRID 1456028 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]=[CH:11][CH:10]=3)[CH3:2].CS(C)=O.[C:21]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1)#[N:22]>O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:28][CH2:27][C:26]4[CH:29]=[CH:30][C:23]([C:21]#[N:22])=[CH:24][CH:25]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 826084-(Aminomethyl)benzonitrileHCID 158169081-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 19592223HCID 19592223, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (1.0 g, 4.3 mmol), DMSO (3 ml) and 4-cyanobenzylamine (1.2 g, 9 mmol) was heated on a steam bath for 3 hours, then was allowed to sit at room temperature overnight. The reaction mixture was poured into water and an oil separated. The oil was extracted with hot 10% ethanol/ethyl acetate, washed with water, and the organic layer was dried and evaporated. The residue was crystallized from ether/ethyl acetate and then was purified by recrystallization from ethyl acetate/hexane, followed by column chromatography on silca gel eluting with ethyl acetate and finally crystallization of the residue thus obtained from ethyl acetate/hexane to afford 280 mg of 1-ethyl-N-(4-cyanophenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as yellow crystals, m.p. 233°-234° C.

Workup

  1. temperaturewas heated on a steam bath for 3 hours
  2. customan oil separated
  3. extractionThe oil was extracted with hot 10% ethanol/ethyl acetate
  4. washwashed with water
  5. customthe organic layer was dried
  6. customevaporated
  7. customThe residue was crystallized from ether/ethyl acetate
  8. customwas purified by recrystallization from ethyl acetate/hexane
  9. washeluting with ethyl acetate and finally crystallization of the residue
  10. customthus obtained from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b411c34ec87d4d0dbb0969a36db549c0
Source dataset
uspto-grants-1998_12
Patent number
US05843956

Reaction notes

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