Dimethylformamide → HCID 86620039, compound

Participants

Reaction Steps

To a solution of tert-butyl[2-(3-hydroxycarbonyl-benzylsulfanyl)-5-fluoro-benzoimidazol-1-yl]-acetate (Precursor 5-F-H-00b, 44.6 mg, 0.1 mmol) in dry DMF (0.8 ml) are added successively Et3N (21.1 μl, 15.2 mg, 0.15 mmol, 1.5 eq.), HOBt (23.0 mg, 0.15 mmol, 1.5 eq.), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (28.8 mg, 0.15 mmol, 1.5 eq.) and indoline (16.8 μl, 17.9 mg, 0.15 mmol, 1.5 eq.). The reaction mixture is stirred at rt overnight. The solvents are evaporated under reduced pressure, dichloromethane (4 ml) is added and the resulting organic phase is washed once with 2 ml of a 1 M NaHCO3 solution in water and once with 2 ml of a 1 M solution of sodium hydrogen sulfate in water. The acidic aqueous phase was extracted once with dichloromethane (2 ml). The combined organic phase is washed with brine. The solvent is removed under a stream of air and the resulting crude product is dried under high vacuum overnight yielding the title compound (40 mg) in 83% as a light brown oil: tR=1.20 min (LC-3), ESI-MS (pos.): m/z 548.23 [M+H]+, 1H-NMR (CDCl3): δ (ppm) 1.400 (s, 9H, tBu), 2.95 (t, 2H, NCH2CH2Ar), 3.91 (s, 3H, OCH3), 3.95 (t, 2H, NCH2CH2Ar), 4.65 (s, 2H, SCH2), 4.72 (s, 2H, CH2CO2), 6.91-7.19 (m, 7Harom), 7.45 (m, 1Harom), 7.52 (m, 1Harom), 7.64 (m, 1Harom).

Provenance & Evidence