Hydrochloric Acid → HCID 59797235, compound

HRID 34049Notes

Reaction equation

HRID 34049 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:31][CH2:32][CH2:33][O:34]C2CCCCO2)=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[N:10]=[C:9]2/[CH:22]=[CH:23]/[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:5])[CH3:2].Cl.O>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:31][CH2:32][CH2:33][OH:34])=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])[N:10]=[C:9]2/[CH:22]=[CH:23]/[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 597971113-[(E)-2-(4-Fluorophenyl)-vinyl]-4-[2-(tetrahydropyran-2-yloxy)-ethoxy]-1H-indazole-1,5-dicarboxylic Acid 1-tert-butyl Ester 5-ethyl Ester

Product 1

HCID 59797235HCID 59797235, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 147 mg of 3-[(E)-2-(4-fluorophenyl)-vinyl]-4-[2-(tetrahydropyran-2-yloxy)-ethoxy]-1H-indazole-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester in 1.5 mL of tetrahydrofuran was added 1.5 mL of 2N hydrochloric acid, and stirred at room temperature for 19 hours. Thereafter, the reaction solution was added with water and extracted twice ethyl acetate, and the resultant organic layer was washed once with saturated brine, and dried over magnesium sulfate. The solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography, to afford 87.1 mg of the title compound as a colorless oil.

Workup

  1. extractionextracted twice ethyl acetate
  2. washthe resultant organic layer was washed once with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe crude product was purified
  6. customseparated by silica gel column chromatography

Sources & evidence

ORD record
ord-dadf4429ce544c138b3aeb1a205cd059
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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