Hydrochloric Acid → HCID 59569034, compound

HRID 1517189Notes

Reaction equation

HRID 1517189 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[CH2:17][S:16][C:15](=[O:18])[N:14]([CH2:19][CH2:20][O:21]C4CCCCO4)[N:13]=3)=[CH:11][C:6]=2[N:5]=[C:4]1[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=1)[CH3:2].Cl>CO.C(=O)([O-])O.[Na+]>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[CH2:17][S:16][C:15](=[O:18])[N:14]([CH2:19][CH2:20][OH:21])[N:13]=3)=[CH:11][C:6]=2[N:5]=[C:4]1[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59569012HCID 59569012, compound

Product 1

HCID 59569034HCID 59569034, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

200 mg (0.40 mM) of 5-[1-ethyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-3,6-dihydro-2H-1,3,4-thiadiazin-2-one and 50 μl (0.6 mM) of 37% hydrochloric acid in 2 ml of methanol are stirred for 16 hours at room temperature. The solvent is evaporated off under vacuum and the residue obtained is taken up in aqueous sodium hydrogen carbonate solution. The resulting mixture is extracted with ethyl acetate and the organic phase is washed with demineralised water and then dried over anhydrous sodium sulfate. The solvent is evaporated off under vacuum to give an oil, which is purified by chromatography on silica, using a dichloromethane/acetone mixture (90/10) as eluent, to give 119 mg of 5-[1-ethyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]-3-(2-hydroxyethyl)-3,6-dihydro-2H-1,3,4-thiadiazin-2-one in the form of an oil that crystallises.

Workup

  1. customThe solvent is evaporated off under vacuum
  2. customthe residue obtained
  3. extractionThe resulting mixture is extracted with ethyl acetate
  4. washthe organic phase is washed with demineralised water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent is evaporated off under vacuum
  7. customto give an oil, which
  8. customis purified by chromatography on silica

Sources & evidence

ORD record
ord-f9b8040052f84f36b98caa35e687f4d0
Source dataset
uspto-grants-2012_07
Patent number
US08232272B2

Reaction notes

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