Dimethyl Sulfoxide → HCID 21217687, compound

HRID 375874Notes

Reaction equation

HRID 375874 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) was stirred at room temperature for 20 minutes, then ethyl 2-bromopropionate (0.2 ml) was added and the mixture was stirred overnight. The reaction mixture was poured into 10 volumes of water, extracted with CH2Cl2 (2×10 ml) and the aqueous layer was acidified with acetic acid. A precipitate formed which was collected by filtration, dissolved in methanol and filtered. The filtrate was allowed to stand and the product which precipitated was 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 was stirred overnight
  2. extractionextracted with CH2Cl2 (2×10 ml)
  3. customA precipitate formed which
  4. filtrationwas collected by filtration
  5. dissolutiondissolved in methanol
  6. filtrationfiltered
  7. customthe product which precipitated
  8. filtrationwas collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-8883fcc5163c44838e0a28278ffd7058
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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