Water → HCID 87238501, Verbindung

Triethylamine (0.182 ml, 1.3 mmol) was added dropwise to a stirred solution of (S)-2-[5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-1H-indol-3-yl]ethyl alcohol (0.20 g, 0.77 mmol), in anhydrous THF (12 ml). The solution was cooled to 0° C. and methane sulphonyl chloride (0.095 ml, 1.2 mmol) added dropwise. The mixture was warmed to room temperature and stirred for 1 h before filtering and evaporating the filtrate in vacuo. The residue was taken up into dichloromethane (50 ml), washed with water (×2) and dried (MgSO4). The solvent was removed in vacuo to give the desired mesylate (0.305 g) which was used without further purification. Potassium carbonate (0.159 g, 1.15 mmol) and sodium iodide (0.115 g, 0.767 mmol) were added successively to a stirred solution of the preceding mesylate (0.305 g, 0.90 mmol) in anhydrous DMF (20 ml). A solution of (3R)-N-(H)-3-[N-(S)-α-methylbenzyl-N-methyl]aminomethylpyrrolidine (0.286 g, 1.31 mmol), in DMF (5 ml), was then added and the mixture heated at 70° C. for 18 h. The reaction mixture was cooled to room temperature and then poured into ethyl acetate (200 ml) and washed with water (×6). The organic layer was dried (MgSO4) and evaporated in vacuo to give the crude product which was chromatographed on silica gel eluting with CH2CO2 /MeOH/NH3 (70:8:1) to give the title-indole (59mg, 14%). The 3.0 hydrogen oxalate hemihydrate salt was prepared, mp 85-90° C. (Hygroscopic), (Found: C, 55.26; H, 5.98; N, 7.60. C28H36N4O2. 3.0 (C2H2O4). 0.5 H2O requires C, 55.21; H, 5.86; N, 7.57%), m/e461 (M+1)+, δ (360 MHz, D6 -DMSO) 1.41 (3H, d, J=6.8Hz, Me), 1.58-1.70 (1H, m, CH of CH2), 2.07-2.20 (1H, m, CH of CH2), 2.27 (3H, s, Me), 2.50-4.24 (17H, m, 3 of CH and 7 of CH2), 6.98 (1H, d, J=8.4Hz, Ar--H), 7.21 (1H, s, Ar--H), 7.26-7.44 (7H, m, Ar--H), 7.80 (1H, s, Ar--H), 10.90 (1H, s, NH).