Acetonitrile → HCID 67314660, compound

HRID 1012212Notes

Reaction equation

HRID 1012212 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]2[S:13][C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)=[N:11][C:10]2=[O:21])=[CH:4][C:3]=1[O:22][CH3:23].CC#N.[CH2:27](Cl)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[CH2:27]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]2[S:13][C:12]([N:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]3)=[N:11][C:10]2=[O:21])=[CH:4][C:3]=1[O:22][CH3:23])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 4979696HCID 4979696, compound

Product 1

HCID 67314660HCID 67314660, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a N2-purged flask was added ′5-[1-(4-Hydroxy-3-methoxy-phenyl)-methylidene]-2-(4-methyl-piperazin-1-yl)thiazol-4-one (57 mg, 0.17 mmol), MeCN (5 mL), benzyl chloride (30 μL, 1.5 equiv), and K2CO3 (70 mg, 3 equiv). The reaction mixture was stirred at 70° C. for 6 h. The reaction mixture was diluted with EtOAc (100 mL), and the excess K2CO3 was removed by filtration through a fritted glass funnel. The product solution was washed with aq NH4Cl (50 mL×2) and H2O (50 mL). The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was chromatographed (SiO2, DCM/MeOH 100:0 to 92:8) to provide pure title compound (20 mg, 28% yield). 1H NMR (DMSO-d6) δ 7.66 (1H, s), 7.44-7.52 (5H, m), 7.29 (1H, s), 7.23-724 (2H, m), 5.22 (2H, s), 3.96 (2H, t, J=4.6 Hz), 3.89 (3H, s), 3.70 (2H, t, J=4.6 Hz), 2.48-2.52 (4H, m), 2.29 (3H, s); MS (ESI) 424 (MH+).

Workup

  1. customTo a N2-purged flask
  2. customthe excess K2CO3 was removed by filtration through a fritted glass funnel
  3. washThe product solution was washed with aq NH4Cl (50 mL×2) and H2O (50 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was chromatographed (SiO2, DCM/MeOH 100:0 to 92:8)

Sources & evidence

ORD record
ord-bcde48b544f64da08408b84ff020fb35
Source dataset
uspto-grants-2011_07
Patent number
US07977489B2

Reaction notes

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