Dimethyl Sulfoxide → HCID 21217687, compound

HRID 1586158Notes

Reaction equation

HRID 1586158 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([OH:24])=[CH:11][CH:10]=3)[CH3:2].CS(C)=O.[OH-].[K+].Br[CH:32]([CH3:38])[C:33]([O:35]CC)=[O:34]>O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([O:24][CH:32]([C:33]([OH:35])=[O:34])[CH3:38])=[CH:11][CH:10]=3)[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 79040Ethyl 2-bromopropionateHCID 9818690HCID 9818690, compound

Product 1

HCID 21217687HCID 21217687, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-ethyl-6-hydroxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine (0.5 g, 1.5 mmol), DMSO (5 ml) and KOH (0.5 g) is stirred at room temperature for 20 minutes, then ethyl 2-bromopropionate (0.2 ml) is added, and the mixture is stirred overnight. The reaction mixture is poured into 10 volumes of water, extracted with CH2Cl2 (2×10 ml), and the aqueous layer is acidified with acetic acid. A precipitate forms which is collected by filtration, dissolved in methanol and filtered. The filtrate is allowed to stand, and the product that precipitates is collected by filtration and dried to afford 180 mg of 1-ethyl-6-(1-carboxyethoxy)-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine. 1/4 Hydrate, m.p. 280° C. (dec.).

Workup

  1. stirringthe mixture is stirred overnight
  2. extractionextracted with CH2Cl2 (2×10 ml)
  3. filtrationA precipitate forms which is collected by filtration
  4. dissolutiondissolved in methanol
  5. filtrationfiltered
  6. customthe product that precipitates
  7. filtrationis collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-011de5a12c8f4317a38c7ce00d2c61a8
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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