2,2-Diethoxy-N,N-dimethylethanamine

Colorless liquid

The mixture of homocoupling product 2i (0.5 mmol), NaOEt (340.25 mg, 5.0 mmol) and DMSO (1.0 mL) was added into a 35 ml pressure-resistant vial under air atmosphere. The mixture was heated to 120oC and stirred for 5h. After being cooled to ambient temperature, the reaction mixture was diluted with EtOAc (60 mL) and washed with H2O (2×30 mL). The aqueous phase was extracted with EtOAc (2×30 mL), and the combined organic phase was dried over anhydrous Na2SO4, filtered and concentrated under the reduced pressure. The residue was purified by silica gel column directly to give the product 3i (Yield 82%). The spectra of 3i were in accordance with those reported in the literature3. Then 16.1mg (1.0 mmol) (dimethylamino)acetaldehyde diethyl acetal was added in the refluxing mixture of 30 mg (0.10 mmol) biindole 3i with the 3ml of AcOH solvent. The resulting mixture was refluxed for 2 h, then cooled to room temperature, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give tjipanazole D (4i) with 65% yield (21.1 mg). The spectra of 4i were in accordance with those reported in the literature3, 4, 5.General procedure: Dimethylaminoacetaldehyde diethyl acetal (5 mmol) was added to a solution of 7 (0.5 mmol) in AcOH (5mL) at room temperature, and the mixture was heated at 100 C. After 1 h, the mixture was gradually cooled to room temperature. The mixture was diluted with AcOEt (100 mL), washed with saturated NaHCO3 solution and brine, and dried over MgSO4. The solvent was removed, and the residue was separated by silica gel column chromatography with hexane/AcOEt (5:1) to give 3, 4 and 8.General procedure: Dimethylaminoacetaldehyde diethyl acetal (5 mmol) was added to a solution of 7 (0.5 mmol) in AcOH (5mL) at room temperature, and the mixture was heated at 100 °C. After 1 h, the mixture was gradually cooled to room temperature. The mixture was diluted with AcOEt (100 mL), washed with saturated NaHCO3 solution and brine, and dried over MgSO4. The solvent was removed, and the residue was separated by silica gel column chromatography with hexane/AcOEt (5:1) to give 3, 4 and 8.

Molecular Weight:161.24
XLogP3:0.9
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:161.141578849
Monoisotopic Mass:161.141578849
Topological Polar Surface Area:21.7
Heavy Atom Count:11
Complexity:80.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes