Hydrochloric Acid → HCID 22097533, compound

HRID 1456016Notes

Reaction equation

HRID 1456016 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].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1.CS(C)=O.Cl>CO.C(OCC)(=O)C>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:24][CH2:23][C:22]4[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[CH:20][CH:21]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 754524-MethoxybenzylamineHCID 158169081-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 22097533HCID 22097533, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 1-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (10 g, 0.043 mol), 4-methoxybenzylamine (13.0 g, 0.095 mol) and DMSO (75 ml) was heated at reflux overnight and then was allowed to stand for about 2 days. The reaction mixture was poured into ice-water and the resulting gum was treated with ethyl acetate. The product which oiled out of the ethyl acetate was separated and then was dissolved in CH2Cl2. The CH2Cl2 layer was washed with water, then brine and then was dried over MgSO4 and evaporated under reduced pressure. The residue was dissolved in CH2Cl2 and purified by column chromatography on silica gel eluting with CH2Cl2 to afford the product as the free base. The free base was dissolved in methanol and then was treated with methanolic HCl. A precipitate formed which was collected by filtration, washed with ether and dried in vacuo at 50° C. to afford 12.4 g of 1-ethyl-N-(4-methoxy phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine.HCl.1/2 H2O, m.p. 179°-180° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customwas separated
  4. dissolutionwas dissolved in CH2Cl2
  5. washThe CH2Cl2 layer was washed with water
  6. dry with materialbrine and then was dried over MgSO4
  7. customevaporated under reduced pressure
  8. dissolutionThe residue was dissolved in CH2Cl2
  9. custompurified by column chromatography on silica gel eluting with CH2Cl2
  10. customto afford the product as the free base
  11. customA precipitate formed which
  12. filtrationwas collected by filtration
  13. washwashed with ether
  14. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-82d224c8acf04e368744daa448c0abda
Source dataset
uspto-grants-1998_12
Patent number
US05843956

Reaction notes

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