Hydrochloric Acid → HCID 58516119, compound

HRID 1945229Notes

Reaction equation

HRID 1945229 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[C:6]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][C:17]=2[Cl:26])[CH:5]=1.[CH3:27]I.[OH-].[Na+].Cl>CN(C=O)C.CO>[Cl:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[C:6]([N:15]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:23])=[O:24])=[CH:18][C:17]=2[Cl:26])[CH3:27])[CH:5]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 11315286HCID 11315286, compound

Product 1

HCID 58516119HCID 58516119, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% disp. oil, 0.11 g) was added to a solution of the product from example 31 (0.5 g) in DMF (5 ml) and stirred at RT for 10 min. Methyl iodide (1 ml) was added, stirred for 5 h then methanol (1 ml) added followed by 1M sodium hydroxide solution (3 ml). After stirring for a further 20 h the mixture was acidified with 2M hydrochloric acid and extracted with ethyl acetate. The organics were washed with brine, dried and evaporated under reduced pressure. The residue was purified by RPHPLC, yield 0.21 g.

Workup

  1. stirringstirred for 5 h
  2. stirringAfter stirring for a further 20 h the mixture
  3. extractionextracted with ethyl acetate
  4. washThe organics were washed with brine
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue was purified by RPHPLC, yield 0.21 g

Sources & evidence

ORD record
ord-8b5577f528184aeea8d57c4205d13a6d
Source dataset
uspto-grants-2013_03
Patent number
US08394986B2

Reaction notes

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