Hydrochloric Acid → HCID 178483387, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(3-(3-(dimethylamino)propyl)-1-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide (50 mg, 0.1 mmol) and anisole (23 μL, 0.2 mmol) in 7.5 mL trifluoroacetic acid was stirred at room temperature for 2 hours then heated at 60° C. for 22 hours. A TLC analysis indicated that only starting material is present. The mixture was concentrated and treated with 3N HCl and ethanol (5 mL) then heated at 60° C. for 4 hours. The yellow solution was treated with saturated NaHCO3 then extracted with 3×20 mL CH2Cl2. The combined organic layers were dried with MgSO4, filtered and concentrated to give a yellow residue. This residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2 to give a light yellow solid. This compound was dissolved in CH2Cl2 (5 mL) and treated with 1 mL of a 1M HCl solution in Et2O to form a precipitate. The slurry was concentrated to give a yellow solid (22 mg, 51.3%). An HPLC analysis indicated that the product is >99% pure. An HPLC analysis indicated that the product is >99% pure. 1H-NMR (CD3OD) δ: 7.96-7.95 (d, J=4.5 Hz, 2H), 7.31 (pseudo t, J=4.2 Hz, 1H), 7.24 (br s, 1H), 7.17 (dd, J=1.5, 8.1 Hz, 1H), 7.00 (d, J=5.9 Hz, 1H), 3.17-3.10 (m, 2H), 2.85 (s, 6H), 2.91-2.83 (m, 2H) 2.67-2.60 (m, 1H), 1.91-1.56 (m, 4H).

Provenance & Evidence