Hydrochloric Acid → HCID 22097533, compound

HRID 1458732Notes

Reaction equation

HRID 1458732 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 AcetateSolvent

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) is heated at reflux overnight and then is allowed to stand for about 2 days. The reaction mixture is poured into ice water, and the resulting gum is treated with ethyl acetate. The product that oils out of the ethyl acetate is separated and then is dissolved in CH2Cl2. The CH2Cl2 layer is washed with water, then brine and then is dried over MgSO4 and evaporated under reduced pressure. The residue is 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 is dissolved in methanol, and then is treated with methanolic HCl. A precipitate forms which is 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. temperatureis heated
  2. temperatureat reflux overnight
  3. customThe product that oils out of the ethyl acetate is separated
  4. dissolutionis dissolved in CH2Cl2
  5. washThe CH2Cl2 layer is washed with water
  6. dry with materialbrine and then is dried over MgSO4
  7. customevaporated under reduced pressure
  8. dissolutionThe residue is dissolved in CH2Cl2
  9. custompurified by column chromatography on silica gel eluting with CH2Cl2
  10. customto afford the product as the free base
  11. filtrationA precipitate forms which is collected by filtration
  12. washwashed with ether
  13. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-d4d91ad215bb48b2960867fb2fb53068
Source dataset
uspto-grants-1998_12
Patent number
US05852035

Reaction notes

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