Hydrochloric Acid → HCID 178434498, compound

HRID 1792542Notes

Reaction equation

HRID 1792542 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[CH:5][N:4](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:3]=1.Cl.[OH-].[Na+].C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C.CO.O1CCCC1>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[CH:5][NH:4][N:3]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 135763128HCID 135763128, compound

Product 1

HCID 178434498HCID 178434498, compoundYield 76%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9.5 mg 4-[6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-quinolyl]phenol obtained in Example 153, 0.13 mL of 5 N hydrochloric acid, 1 mL tetrahydrofuran, and 1 mL methanol was stirred overnight at room temperature. The reaction solution was cooled and then neutralized with 2 N aqueous sodium hydroxide and an aqueous saturated sodium bicarbonate solution. Then, ethyl acetate and water were added thereto, the organic layer was separated, the solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 4 mg of the title compound as a colorless amorphous.

Workup

  1. temperatureThe reaction solution was cooled
  2. customthe organic layer was separated
  3. customthe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-94404d995661477994379b6f2373c5b6
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

Loading…