Dimethyl Sulfide → HCID 57476279, compound

HRID 1960464Notes

Reaction equation

HRID 1960464 reaction equation
C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C([S:43][CH:44]([CH2:71][N:72]1[CH2:77][CH2:76][O:75][CH2:74][CH2:73]1)[CH2:45][NH:46][C:47]([C:49]1[NH:50][C:51]2[C:56]([CH:57]=1)=[C:55]([CH3:58])[CH:54]=[CH:53][C:52]=2[N:59]([S:61]([C:64]1[C:65]([Cl:70])=[N:66][CH:67]=[CH:68][CH:69]=1)(=[O:63])=[O:62])[CH3:60])=O)C1C=CC=CC=1.CSC.C(=O)([O-])O.[Na+]>C(#N)C>[Cl:70][C:65]1[C:64]([S:61]([N:59]([CH3:60])[C:52]2[CH:53]=[CH:54][C:55]([CH3:58])=[C:56]3[C:51]=2[NH:50][C:49]([C:47]2[S:43][CH:44]([CH2:71][N:72]4[CH2:77][CH2:76][O:75][CH2:74][CH2:73]4)[CH2:45][N:46]=2)=[CH:57]3)(=[O:62])=[O:63])=[CH:69][CH:68]=[CH:67][N:66]=1

Participants

7

Reactant 5

HCID 1068Dimethyl SulfideHCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 59135766HCID 59135766, compound

Product 1

HCID 57476279HCID 57476279, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of triphenylphosphine oxide (1.95 g) and acetonitrile (20 mL) was slowly added trifluoromethanesulfonic anhydride (0.59 mL) at 0° C., and the mixture was stirred for 10 min. N-[2-(Benzylthio)-3-Morpholinopropyl]-7-[[(2-chloropyridin-3-yl) sulfonyl](methyl)amino]-4-methyl-1H-indole-2-carboxamide (1.10 g) and dimethylsulfide (0.20 mL) were added. The reaction mixture was stirred at 0° C. for 15 min. Saturated aqueous sodium hydrogencarbonate was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The residue was subjected to basic silica gel column chromatography to give the title compound (0.69 g, yield 76%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (3:1, volume ratio). melting point 151-153° C.

Workup

  1. customat 0° C.
  2. stirringThe reaction mixture was stirred at 0° C. for 15 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-02709f4c20464733953a43dc05d91693
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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