Methanol → HCID 22048183, compound

HRID 481124Notes

Reaction equation

HRID 481124 reaction equation
[Cl:1][C:2]1[C:3]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[C:4]2[C:18]3[CH2:19][CH2:20][C:21](=O)[CH2:22][C:17]=3[S:16][C:5]2=[N:6][C:7]=1[CH2:8][N:9]1[C:13](=[O:14])[CH2:12][CH2:11][C:10]1=[O:15].Cl.[NH2:33][OH:34].O.CO>C1COCC1>[Cl:1][C:2]1[C:3]([C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)=[C:4]2[C:18]3[CH2:19][CH2:20]/[C:21](=[N:33]/[OH:34])/[CH2:22][C:17]=3[S:16][C:5]2=[N:6][C:7]=1[CH2:8][N:9]1[C:13](=[O:14])[CH2:12][CH2:11][C:10]1=[O:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 10226154HCID 10226154, compound

Product 1

HCID 22048183HCID 22048183, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the compound obtained in Example 33 (2.0 g), hydroxylamine hydrochloride (673 mg), water (5 ml), methanol (5 ml), and THF (40 ml) was heat under reflux for 2 hours and then evaporated under reduced pressure to remove the solvent. The residue was dissolved in methylene chloride and the resulting solution was washed with a saturated, aqueous solution of sodium hydrogen carbonate and water, dried (MgSO4), and then evaporated under reduced pressure to remove the solvent. The residue was subjected to column chromatography on silica gel to obtain (Z)-1-{[3-chloro-7-(hydroxyimino)-4-(4-methoxyphenyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-2-yl]methyl}-2,5-pyrrolidinedione:

Workup

  1. temperaturewas heat
  2. temperatureunder reflux for 2 hours
  3. customevaporated under reduced pressure
  4. customto remove the solvent
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washthe resulting solution was washed with a saturated, aqueous solution of sodium hydrogen carbonate and water
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure
  9. customto remove the solvent

Sources & evidence

ORD record
ord-8eb94ea0aa3848a4a48994caa408f689
Source dataset
uspto-grants-2003_11
Patent number
US06653476B2

Reaction notes

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