Dimethyl Sulfide → HCID 59135754, compound

HRID 1994938Notes

Reaction equation

HRID 1994938 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]([CH2:69][N:70]1[CH2:75][CH2:74][O:73][CH2:72][CH2:71]1)[CH2:45][NH:46][C:47]([C:49]1[NH:50][C:51]2[C:56]([CH:57]=1)=[CH:55][CH:54]=[CH:53][C:52]=2[N:58]([CH3:68])[S:59]([C:62]1[CH:63]=[N:64][CH:65]=[CH:66][CH:67]=1)(=[O:61])=[O:60])=O)C1C=CC=CC=1.CSC>C(#N)C.ClCCl.C(OCC)(=O)C.[Cl-].[Na+].O>[CH3:68][N:58]([C:52]1[CH:53]=[CH:54][CH:55]=[C:56]2[C:51]=1[NH:50][C:49]([C:47]1[S:43][CH:44]([CH2:69][N:70]3[CH2:71][CH2:72][O:73][CH2:74][CH2:75]3)[CH2:45][N:46]=1)=[CH:57]2)[S:59]([C:62]1[CH:63]=[N:64][CH:65]=[CH:66][CH:67]=1)(=[O:60])=[O:61]

Participants

9

Reactant 4

HCID 1068Dimethyl SulfideHCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 59135763HCID 59135763, compound

Product 1

HCID 59135754HCID 59135754, compoundYield 11.5%

Reagents, catalysts & solvents 4

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of triphenylphosphine oxide (790 mg) and acetonitrile (15 mL) was added trifluoromethanesulfonic anhydride (238 μL), and the mixture was stirred at 0° C. for 10 min. A solution of N-[2-(benzylthio)-3-morpholinopropyl]-7-[methyl(pyridin-3-ylsulfonyl)amino]-1H-indole-2-carboxamide (410 mg) and dimethylsulfide (52 μL) in acetonitrile (15 mL) and dichloromethane (15 mL) was added to the mixture, and the mixture was stirred at 0° C. for 2 hr. The reaction mixture was diluted with ethyl acetate (100 mL) and saturated brine (100 mL). The organic layer was dried over sodium sulfate, and filtrated, and the filtrate was concentrated. The obtained residue was purified by preparative HPLC to give the title compound (38.3 mg, yield 11%) as a white solid. melting point 234-236° C.

Workup

  1. stirringthe mixture was stirred at 0° C. for 2 hr
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltrated
  4. concentrationthe filtrate was concentrated
  5. customThe obtained residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-1dd0759d4457421d8d72c0ee1ad6ef69
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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