Dimethyl Sulfoxide → HCID 86633104, compound

HRID 1012208Notes

Reaction equation

HRID 1012208 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:4]=1[CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([CH2:11][CH:12]2[S:16][C:15](=S)[NH:14][C:13]2=[O:18])=[CH:9][C:8]=1[O:21][CH3:22].CS(C)=O.IC.[CH3:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>CCOC(C)=O.CC#N>[F:1][C:2]([F:32])([F:31])[C:3]1[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[CH:23][C:4]=1[CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([CH2:11][CH:12]2[S:16][C:15]([N:43]3[CH2:44][CH2:45][N:40]([CH3:39])[CH2:41][CH2:42]3)=[N:14][C:13]2=[O:18])=[CH:9][C:8]=1[O:21][CH3:22]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 531671-MethylpiperazineHCID 86633103HCID 86633103, compound

Product 1

HCID 86633104HCID 86633104, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a flask was added 5-[4-(2,4-bis-trifluoromethyl-benzyloxy)-3-methoxy-benzyl]-2-thioxo-thiazolidin-4-one from Step A (140 mg, 282 μmol), DMSO (1 mL) and iodomethane (2 mL). The reaction solution was allowed to stir under N2 for 3 h. The excess iodomethane was removed in vacuo. To the reaction mixture was added MeCN (6 mL) and N-methyl piperazine (95 μL, 850 μmol). The reaction solution was stirred at 55° C. for 2 h. The reaction solution was then diluted with EtOAc (200 mL), washed with aq. NH4Cl and water, dried over Na2SO4 and concentrated. The crude material was chromatographed (SiO2, DCM/MeOH 100:0 to 90:10) to provide title compound (55 mg, 35% yield). 1H NMR (CDCl3) δ 8.10 (1H, d, J=8.1 Hz), 7.92 (1H, s), 7.83 (1H, d, J=8.1 Hz), 6.83 (1H, s), 6.73 (2H, br s), 5.36 (2H, s), 4.46 (1H, dd, J1=3.6 Hz, J2=10.4 Hz), 3.96 (2H, t, J=4.9 Hz), 3.90 (3H, s), 3.57 (1H, dd, J=3.6 Hz, J2=14.3 Hz), 3.49 (2H, t, J=4.9 Hz), 2.92 (1H, dd, J1=10.4 Hz, J2=14.3 Hz), 2.46 (4H, m), 2.32 (3H, s); MS (ESI) 562 (MH+).

Workup

  1. customThe excess iodomethane was removed in vacuo
  2. stirringThe reaction solution was stirred at 55° C. for 2 h
  3. washwashed with aq. NH4Cl and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude material was chromatographed (SiO2, DCM/MeOH 100:0 to 90:10)

Sources & evidence

ORD record
ord-10407c7ba2e54754a0975abb84a6cf76
Source dataset
uspto-grants-2011_07
Patent number
US07977489B2

Reaction notes

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