Thioanisole → HCID 68464080, compound

HRID 1960503Notes

Reaction equation

HRID 1960503 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:36]([N:39]1[CH2:44][CH2:43][N:42]([CH2:45][CH:46]([S:79]CC2C=CC=CC=2)[CH2:47][NH:48][C:49]([C:51]2[NH:52][C:53]3[C:58]([CH:59]=2)=[CH:57][C:56]([O:60][CH2:61][CH2:62][CH2:63][S:64]([CH3:67])(=[O:66])=[O:65])=[CH:55][C:54]=3[N:68]([CH3:78])[S:69]([C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][N:73]=2)(=[O:71])=[O:70])=O)[CH2:41][CH2:40]1)(=[O:38])[CH3:37].C1(SC)C=CC=CC=1>ClCCl.C(OCC)(=O)C>[C:36]([N:39]1[CH2:44][CH2:43][N:42]([CH2:45][CH:46]2[S:79][C:49]([C:51]3[NH:52][C:53]4[C:58]([CH:59]=3)=[CH:57][C:56]([O:60][CH2:61][CH2:62][CH2:63][S:64]([CH3:67])(=[O:66])=[O:65])=[CH:55][C:54]=4[N:68]([CH3:78])[S:69]([C:72]3[CH:77]=[CH:76][CH:75]=[CH:74][N:73]=3)(=[O:70])=[O:71])=[N:48][CH2:47]2)[CH2:41][CH2:40]1)(=[O:38])[CH3:37]

Participants

7

Reactant 4

HCID 7520ThioanisoleHCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 67486861HCID 67486861, compound

Product 1

HCID 68464080HCID 68464080, compoundYield 37.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of triphenylphosphine oxide (0.38 g) in dichloromethane (3 mL) Was slowly added trifluoromethanesulfonic anhydride (0.23 mL) under ice-cooling, and the mixture was stirred for 30 min. A solution of N-[3-(4-acetylpiperazin-1-yl)-2-(benzylthio)propyl]-7-[methyl(pyridin-2-ylsulfonyl)amino]-5-[3-(methylsulfonyl)propoxy]-1H-indole-2-carboxamide (0.34 g) and thioanisole (0.17 mL) in dichloromethane (5 mL) was added dropwise, and the mixture was stirred for 1 hr under ice-cooling. The reaction solution was diluted with ethyl acetate, washed with aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to basic silica gel column chromatography (ethyl acetate), and the obtained colorless oil was crystallized from ethyl acetate-hexane to give the title compound (109 mg, yield: 37%) as colorless crystals. MS:650(MH+). melting point 165-167° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hr under ice-
  3. temperaturecooling
  4. washwashed with aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe obtained colorless oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7b0fd91ecf834f0c94a91c8fdf5ce410
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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