Dimethyl Sulfoxide → HCID 59000932, compound

HRID 529185Notes

Reaction equation

HRID 529185 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:52]=[CH:51][CH:50]=[C:49]([F:53])[C:13]=1[CH2:14][N:15]1[C:20]2[S:21][C:22]([C:31]3[CH:36]=[CH:35][C:34]([NH:37][C:38]([NH:40][O:41][CH3:42])=[O:39])=[CH:33][CH:32]=3)=[C:23]([CH2:24][N:25]([CH2:27][CH2:28][O:29][CH3:30])[CH3:26])[C:19]=2[C:18](=[O:43])[N:17]([CH2:44][CH:45]([OH:47])[CH3:46])[C:16]1=[O:48].C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[F:53][C:49]1[CH:50]=[CH:51][CH:52]=[C:12]([F:11])[C:13]=1[CH2:14][N:15]1[C:20]2[S:21][C:22]([C:31]3[CH:32]=[CH:33][C:34]([NH:37][C:38]([NH:40][O:41][CH3:42])=[O:39])=[CH:35][CH:36]=3)=[C:23]([CH2:24][N:25]([CH2:27][CH2:28][O:29][CH3:30])[CH3:26])[C:19]=2[C:18](=[O:43])[N:17]([CH2:44][C:45](=[O:47])[CH3:46])[C:16]1=[O:48]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 59000874HCID 59000874, compound

Product 1

HCID 59000932HCID 59000932, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of oxalyl chloride (0.20 g, 1.58 mmol) in dichloromethane (2 ml) was dropwise added a solution of dimethylsulfoxide (163 mg, 2.09 mmol) in dichloromethane (2 ml) under cooling at −78° C. After stirring for 10 minutes, a solution of the compound (308 mg, 0.5 mmol) obtained in Example 61 in dichloromethane (2 ml) was dropwise added. After stirring for further 30 minutes, triethylamine (0.40 ml, 2.88 mmol) was dropwise added, and the mixture was stirred at 0° C. for 2 hours. To the mixture was added an aqueous solution of ammonium chloride at 0° C., and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated with under reduced pressure. The residue was purified by NH-silica gel (Produced by Fuji Silysia Chemical Ltd.) column chromatography (eluent;ethyl acetate), and the obtained powders was washed with diisopropyl ether and hexane to give the title compound (40.7 mg, 13%) as pale yellow powders.

Workup

  1. stirringAfter stirring for further 30 minutes
  2. stirringthe mixture was stirred at 0° C. for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated with under reduced pressure
  7. customThe residue was purified by NH-silica gel (Produced by Fuji Silysia Chemical Ltd.) column chromatography (eluent;ethyl acetate)
  8. washthe obtained powders was washed with diisopropyl ether and hexane

Sources & evidence

ORD record
ord-4dc6db61487e4dffb47c0f240df1b1c8
Source dataset
uspto-grants-2016_05
Patent number
US09346822B2

Reaction notes

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