Water → HCID 90402499, compound

HRID 522343Notes

Reaction equation

HRID 522343 reaction equation
[S:1](Cl)([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH3:18][N:19]([CH3:36])[CH2:20][CH2:21][S:22][S:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([OH:35])[C:31](F)(F)F)=[CH:26][CH:25]=1.C1N2CCN(CC2)C1.O>C(Cl)Cl>[CH3:18][N:19]([CH3:36])[CH2:20][CH2:21][S:22][S:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([O:35][S:1]([C:4]2[C:16]3[C:8](=[C:9]([N:10]([CH3:12])[CH3:11])[CH:13]=[CH:14][CH:15]=3)[CH:7]=[CH:6][CH:5]=2)(=[O:3])=[O:2])[CH3:31])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 11801Dansyl chlorideHCID 90402495HCID 90402495, compound

Product 1

HCID 90402499HCID 90402499, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dansyl chloride (37.5 mg, 0.13 mmol) dissolved in dry CH2Cl2 (0.5 mL) was added to the crude 1-[4-(2-dimethylamino-ethyldisulfanyl)-phenyl]-2,2,2-trifluoro-ethanol obtained above. To this solution was added dropwise a solution of DABCO (157 mg, 1.4 mmol) dissolved in dry CH2Cl2 (0.25 mL). After 4 hours at room temperature, the reaction mixture was poured into H2O (30 mL) and extracted using ethyl acetate (3×30 mL). The combined organic phases were washed with H2O (3×30 mL), followed by brine (1×30 mL) and then dried over Na2SO4. The organic phase was collected by filtration and concentrated by rotary evaporation. The crude product thus formed was purified by using flash chromatography on silica gel using 0-2% CH2Cl2/MeOH to yield Compound 2 a yellow oil (8 mg). 1H NMR (400 MHz, CD3OD): δ 8.45 (m, 1H), 8.13 (m, 2H), 7.57 (m, 1H), 7.43 (m, 1H), 7.27 (m, 1H), 7.06 (m, 2H), 6.98 (d, J=8.47, 2H), 5.88 (q, J=6.5 Hz, 1H), 2.8 (s, 6H), 2.78 (m, 2H), 2.57 (m, 2H), 2.21 (s, 6H); 19F NMR (376 MHz, CH3OD): δ −78.1 (d, J=6.5 Hz).

Workup

  1. customobtained above
  2. extractionextracted
  3. washThe combined organic phases were washed with H2O (3×30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationThe organic phase was collected by filtration
  6. concentrationconcentrated by rotary evaporation
  7. customThe crude product thus formed
  8. customwas purified

Sources & evidence

ORD record
ord-f67c41bf67704fa2a0c4b84fd6c7405f
Source dataset
uspto-grants-2016_05
Patent number
US09329185B2

Reaction notes

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