Water → HCID 136090584, compound

HRID 1382896Notes

Reaction equation

HRID 1382896 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[NH:18][N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:32][CH2:33][CH2:34][C:35]([O:37]CC)=[O:36].O>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])[N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18474Ethyl 4-chlorobutyrateHCID 178440702HCID 178440702, compound

Product 1

HCID 136090584HCID 136090584, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 9.7 g of the compound of Example 1 in 70 ml of dimethylformamide are added 5.5 g of potassium carbonate and 6 g of ethyl 4-chlorobutyrate, and the mixture is stirred at 60° C. for 21 hours. The reaction mixture is poured into water and extracted with ethyl acetate. The extract is washed with water, dried and concentrated. To a solution of the residue in 100 ml of 80 % methanol is added 3 g of potassium hydroxide, and the mixture is stirred at room temperature for two hours. After completion of the reaction, the methanol is distilled off under reduced pressure and the residue is dissolved into water and the aqueous solution is acidified with dilute hydrochloric acid. The precipitated crystals are collected by filtration and then recrystallizing from ethanol to give 8.3 g of 4-[3-(3,5-di-tertiary butyl-4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]butyric acid as pale yellow crystals, melting at 192°-194° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with water
  3. customdried
  4. concentrationconcentrated
  5. additionTo a solution of the residue in 100 ml of 80 % methanol is added 3 g of potassium hydroxide
  6. stirringthe mixture is stirred at room temperature for two hours
  7. customAfter completion of the reaction
  8. distillationthe methanol is distilled off under reduced pressure
  9. dissolutionthe residue is dissolved into water
  10. filtrationThe precipitated crystals are collected by filtration
  11. customrecrystallizing from ethanol

Sources & evidence

ORD record
ord-f9514fb9281a4f60a8eada2966918893
Source dataset
uspto-grants-1989_02
Patent number
US04808620

Reaction notes

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