Dimethyl Sulfoxide → HCID 10299623, compound

HRID 1830842Notes

Reaction equation

HRID 1830842 reaction equation
CS(C)=[O:3].[C:5](Cl)(=[O:9])[C:6](Cl)=O.C([O:18][CH:19]1[CH2:38][C:23]2[S:24][C:25]([NH2:37])=[C:26]([C:27](=O)[C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[C:22]=2[CH2:21][C:20]1([CH3:40])[CH3:39])C1C=CC=CC=1.C([N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])C.[CH2:48]([Cl:50])Cl>O>[Cl:50][C:48]1[C:27]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[C:26]2[C:22]3[CH2:21][C:20]([CH3:40])([CH3:39])[C:19](=[O:18])[CH2:38][C:23]=3[S:24][C:25]2=[N:37][C:47]=1[CH2:46][N:43]1[C:5](=[O:9])[CH2:6][CH2:45][C:44]1=[O:3]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6344Dichloromethane3×HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22048221HCID 22048221, compound

Product 1

HCID 10299623HCID 10299623, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-30 °C

Procedure

A solution of dimethyl sulfoxide (30 mg) in methylene chloride (1 ml) was added to a solution of oxalyl chloride (37 mg) in methylene chloride (4 ml) at −78° C. under a nitrogen atmosphere. After stirring at the same temperature for 1 hour, a solution of the compound obtained in Example 13 (70 mg) in methylene chloride (4 ml) was added thereto and then the stirring was continued at −78° C. for 1 hour. The reaction temperature was raised to at −30° C. and, after stirring at 30 minutes, triethylamine (150 μl) was added thereto and then the solution temperature was slowly raised to at 0° C. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with 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 1-{[3-chloro-4-(4-methoxyphenyl)-6,6-dimethyl-7-oxo-5,6,7,8-tetrahydro [1]benzothieno[2,3-b]pyridin-2-yl]methyl}-2,5-pyrrolidinedione:

Workup

  1. waitthe stirring was continued at −78° C. for 1 hour
  2. stirringafter stirring at 30 minutes
  3. temperaturethe solution temperature was slowly raised to at 0° C
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customto remove the solvent

Sources & evidence

ORD record
ord-38a2ba9379ee4f62872eab064080b92f
Source dataset
uspto-grants-2006_06
Patent number
US07067527B2

Reaction notes

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