Dichloromethane → 4'-[(2-Butyl pyrazolo(1,5-a)pyridin-3-yl) methyl](1,1'-biphenyl) 2-carboxylic acid

HRID 37208Notes

Reaction equation

HRID 37208 reaction equation
[CH2:1]([C:5]1[C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:22]([C:27]([O:29]C(C)(C)C)=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)=[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][N:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4].C(Cl)Cl.FC(F)(F)C(O)=O>[OH-].[Na+].CCOCC>[CH2:1]([C:5]1[C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:22]([C:27]([OH:29])=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)=[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][N:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 190324701,1-Dimethylethyl 4'-[(2-butyl pyrazolo (1,5-a)pyridin-3-yl)methyl]-(1,1-biphenyl) 2-carboxylate

Product 1

HCID 442111764'-[(2-Butyl pyrazolo(1,5-a)pyridin-3-yl) methyl](1,1'-biphenyl) 2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 1 g of the product of Example 6, 20 ml of methylene chloride and 4 ml of trifluoroacetic acid was stirred at room temperature for 4 hours and the solvent and the reagent were eliminated at 30° C. under reduced pressure. The residue was taken up in a mixture of 40 ml of 1N sodium hydroxide and 20 ml of ether and extracted with 1N sodium hydroxide. The aqueous phase was acidified with concentrated hydrochloric acid and extracted with ether after saturation with sodium chloride. After drying and filtering, the solvent was eliminated at 50° C. under reduced pressure.

Workup

  1. customwere eliminated at 30° C. under reduced pressure
  2. extractionextracted with 1N sodium hydroxide
  3. extractionextracted with ether after saturation with sodium chloride
  4. customAfter drying
  5. filtrationfiltering
  6. customwas eliminated at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-855164ca016e424e93e15d8fd1937817
Source dataset
uspto-grants-1995_05
Patent number
US05420138

Reaction notes

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