Dimethylformamide → HCID 76618661, compound

HRID 1012201Notes

Reaction equation

HRID 1012201 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:12]=[CH:11][C:10]([CH:13]=[C:14]2[S:18]C(=S)[NH:16][C:15]2=[O:20])=[CH:9][C:8]=1[O:21][CH3:22].IC.[CH3:35]N(C=O)C.[CH3:40][N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1>CCOC(C)=O>[F:1][C:2]([F:31])([F:32])[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:12]=[CH:11][C:10]([CH:13]=[C:14]2[S:18][C:40]([N:41]3[CH2:46][CH2:45][N:44]([CH3:35])[CH2:43][CH2:42]3)=[N:16][C:15]2=[O:20])=[CH:9][C:8]=1[O:21][CH3:22]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 531671-MethylpiperazineHCID 72994854HCID 72994854, compound

Product 1

HCID 76618661HCID 76618661, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a flask purged with N2 was added ′5-[1-[4-(2,4-Bis-trifluoromethyl-benzyloxy)-3-methoxy-phenyl]-methylidene]-2-thioxo-thiazolidin-4-one, (1.12 g, 2.27 mmol), iodomethane (5.5 mL, 88 mmol) and DMF (35 mL). The solution was al lowed to stir at 40° C. for 20 h. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in MeCN (25 mL). To the mixture was added 1-methyl piperazine (0.76 mL, 6.8 mmol), and the solution was stirred at 65° C. for 2 h. The solution was then diluted with EtOAc (150 mL), washed with sat NH4Cl (70 mL×2), dried over Na2SO4, filtered and concentrated. The crude material was chromatographed (SiO2 DCM/MeOH 100:0 to 90:10) to provide the title product (470 mg, 37% yield). 1H NMR (DMSO-d6) δ 8.17 (1H, d, J=8.1 Hz), 8.11 (1H, s), 8.02 (1H, d, J=8.1 Hz), 7.61 (1H, s), 7.29 (1H, d, J=2.0 Hz), 7.20 (1H, dd, J=2.0 Hz, J2=8.4 Hz), 7.14 (1H, d, J=8.4 Hz), 5.41 (2H, s), 3.90 (2H, t, J=4.8 Hz), 3.86 (3H, s), 3.65 (2H, t, J=4.8 Hz), 2.43-2.50 (4H, m), 2.24 (3H, s); 19F NMR (DMSO-d6) d −59.5, −61.6; MS (ESI) 560 (MH+).

Workup

  1. customTo a flask purged with N2
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in MeCN (25 mL)
  4. stirringthe solution was stirred at 65° C. for 2 h
  5. washwashed
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was chromatographed (SiO2 DCM/MeOH 100:0 to 90:10)

Sources & evidence

ORD record
ord-66b8c95c873045948cf8050d4226bce1
Source dataset
uspto-grants-2011_07
Patent number
US07977489B2

Reaction notes

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