Hydrochloric Acid → HCID 178516578, compound

HRID 1947183Notes

Reaction equation

HRID 1947183 reaction equation
[Br:1][C:2]1[C:3]([O:30]COC)=[CH:4][C:5]([O:26]COC)=[C:6]([C:8]2[N:9]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[C:10](=[S:13])[NH:11][N:12]=2)[CH:7]=1.Cl.[OH-].[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[N:9]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[C:10]([SH:13])=[N:11][N:12]=2)[C:5]([OH:26])=[CH:4][C:3]=1[OH:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59829807HCID 59829807, compound

Product 1

HCID 178516578HCID 178516578, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude crystals of 5-(5-bromo-2,4-bis-methoxymethoxy-phenyl)-4-[4-(morpholin-4-yl)-phenyl]-2,4-dihydro-[1,2,4]triazol-3-thione (IM6-S-d01) and a mixed solvent of 5.0 N aqueous hydrochloric acid (1 mL) and ethanol (1 mL) were placed in a test tube and stirred at room temperature for 24 hours. After completing the reaction, the reaction mixture was neutralized with 10 N aqueous sodium hydroxide, and then extracted with ethyl acetate and methylene chloride. The collected organic layer was dried over anhydrous sodium sulfate. After filtration and evaporation, the residue thus obtained was purified by HPLC fractionation to obtain the title compound (SH-d01: 8.6 mg, 34%).

Workup

  1. customthe reaction
  2. extractionextracted with ethyl acetate and methylene chloride
  3. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  4. filtrationAfter filtration and evaporation
  5. customthe residue thus obtained
  6. customwas purified by HPLC fractionation

Sources & evidence

ORD record
ord-fc321ccc5a9a42c18d817f7b87d21760
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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