Nitrogen → HCID 16074767, compound

Participants

Reaction Conditions

Reaction Steps

Sodium Hydride (60% dispersion in oil, 190 mg, 5,2 mmol) was added to an ice-cold solution of 3-(2,4-Dichloro-benzoylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester (2) (1.5 g, 3.69 mmol) in 350 ml of N,N-dimethylformamide in an atmosphere of N2. After 5 min, 2-Iodo-propane (941 mg, 5.54 mmol) was added to the solution and then the reaction mixture was stirred for 30 min at 0° C. and 64 h at room temperature. The mixture was partitioned between ether (200 mL) and water (350 mL) and the organic layer was separated. The aqueous phase was washed twice with ether (2×70 mL) and the combined ether layer was dried (MgSO4), concentrated and the residue was purified by flash chromatography (10% EtOAc/Hexane) to obtain 908 mg (55%) of 3-[(2,4-Dichloro-benzoyl)-isopropyl-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester. NMR 1H (CDCl3, 400 MHz): Rotamere 95/05: 7.54 ppm (dd, 2H, Haro); 7.49-7.35 ppm (m, 3H, Haro); 7.29-7.25 ppm (m, 2H, Haro); 7.15 ppm (d, 1H, Haro); 7.05 ppm (d, 1H, Haro) 5.09 ppm (hex, 1H, N—CH(CH3), major rotamere); 3.99 ppm (hex, N—CH(CH3), minor rotamere); 3.89 ppm (s, 3H); 1.40 ppm (d, 3H, N—CH(CH3), major rotamere); 1.28 ppm (d, N—CH(CH3), minor rotamere); 1.09 ppm (d, 3H, N—CH(CH3), major rotamere); 1.01 ppm (d, N—CH(CH3), minor rotamere).

Provenance & Evidence