Triethylamine → HCID 178448504, compound

HRID 1693635Notes

Reaction equation

HRID 1693635 reaction equation
[CH2:1]([N:5]1[CH2:9][C:8]([CH3:11])([CH3:10])[S:7][C:6]1=[NH:12])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[C:20]12([C:30](Cl)=[O:31])[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2>C1COCC1>[CH2:1]([N:5]1[CH2:9][C:8]([CH3:11])([CH3:10])[S:7]/[C:6]/1=[N:12]\[C:30]([C:20]12[CH2:29][CH:24]3[CH2:23][CH:22]([CH2:28][CH:26]([CH2:25]3)[CH2:27]1)[CH2:21]2)=[O:31])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 666431113-Butyl-5,5-dimethylthiazolidin-2-imine

Product 1

HCID 178448504HCID 178448504, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 2A (149 mg, 0.8 mmol) in THF (10 mL) was added triethylamine (0.4 mL) and adamantane-1-carbonyl chloride (0.2 g, 1 mmol). The mixture was heated to reflux overnight and then concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with 1 M NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (SiO2, 0-100% ethyl acetate:hexanes) to provide 25 mg of the title compound. MS (ESI+) m/z 349 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm 0.92 (t, J=7.3 Hz, 3H), 1.19-1.36 (m, 2H), 1.39 (s, 6H), 1.51-1.61 (m, 2H), 1.61-1.73 (m, 6H), 1.74-1.81 (m, 6H), 1.89-2.02 (m, 3H), 3.40-3.44 (m, 2H), 3.55-3.64 (m, 2H); Anal. Calculated for C20H32N2OS: C, 68.92; H, 9.25; N, 8.04. Found: C, 68.94; H, 8.73; N, 8.02.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with 1 M NaHCO3
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (SiO2, 0-100% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-cfe5283d8e1547b19bb4a7fb683c6ede
Source dataset
uspto-grants-2012_04
Patent number
US08158663B2

Reaction notes

Loading…