HCID 178525893, compound → HCID 178525889, compound

HRID 1746227Notes

Reaction equation

HRID 1746227 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]=1)[S:8][C:7](=[O:19])[C:6]([C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21])=[C:5]2[OH:27]>[OH-].[Na+].[Pd]>[CH2:12]([C:10]1[CH:11]=[CH:2][CH:3]=[C:4]2[C:9]=1[S:8][C:7](=[O:19])[C:6]([C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21])=[C:5]2[OH:27])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 178525893HCID 178525893, compound

Product 1

HCID 178525889HCID 178525889, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14798Sodium HydroxideSolvent

Procedure

[(6-Chloro-4-hydroxy-2-oxo-8-benzyl-2H-thiochromene-3-carbonyl)-amino]-acetic acid (Example 42 a) (70 mg, 0.173 mmol) was dissolved in aqueous sodium hydroxide (870 uL 1M in 8 mL of water) and 10% palladium on carbon (7 mg) was added. The reaction was vacuum-purged and placed under an atmosphere of hydrogen gas and permitted to stir overnight at ambient temperature. Upon completion, the reaction was filtered through a pad of Celite® to remove the palladium catalyst. The product was precipitated with 1N HCl, isolated via filtration and dried to provide the title compound (30 mg.) MS ESI(−) m/e: 368.093 (M−1).

Workup

  1. customThe reaction was vacuum-purged
  2. filtrationUpon completion, the reaction was filtered through a pad of Celite®
  3. customto remove the palladium catalyst
  4. customThe product was precipitated with 1N HCl
  5. customisolated via filtration
  6. customdried

Sources & evidence

ORD record
ord-b07aa3c4a8f740558f3f727352e4c013
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

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