Hydrochloric Acid → HCID 86721225, compound

HRID 1750385Notes

Reaction equation

HRID 1750385 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:11]=[CH:10][C:9]=2[C:19]2[S:20][CH:21]=[C:22]([CH2:24][C:25]([O:27]CC)=[O:26])[N:23]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:11]=[CH:10][C:9]=2[C:19]2[S:20][CH:21]=[C:22]([CH2:24][C:25]([OH:27])=[O:26])[N:23]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86721226HCID 86721226, compound

Product 1

HCID 86721225HCID 86721225, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the compound (220 mg, 0.540 mmol) obtained in step 5 and 1N aqueous sodium hydroxide solution (1.08 mmol, 1.08 mL) in ethanol (5.0 mL) was heated under reflux for 1 hr. The reaction mixture was cooled to room temperature, and concentrated hydrochloric acid was added until the mixture became pH 6. The mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent; 33% ethyl acetate/hexane) to give {2-[5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl]-1,3-thiazol-4-yl}acetic acid (140 mg, 68%) as a yellow powder.

Workup

  1. temperatureunder reflux for 1 hr
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (solvent; 33% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9bf235b702ef45d39693a693b277e385
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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