Methanesulfonic acid, aminoimino- → HCID 178481554, compound

Participants

Reaction Steps

To a magnetically stirred solution of 6 mgs of 1-methyl-4-(2-carboxyethyl)-7-(5-amino-1-pentynyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione trifluoracetate (0.017 mmol) in 1.0 mL 10% potassium bicarbonate was added 31.0 mgs of formamidine sulfonic acid (0.25 mmol). After 30 minutes, the reaction mixture was quenched with 0.5 mL acetic acid and concentrated in vacuo. The resulting residue was diluted with 2 mL water and purified by high pressure liquid chromatography, using a 1/2" C-18 reverse-phase column, eluting with a solvent gradient of 10:90 methanol(0.1% trifluoracetic acid)/water (0.1% trifluoracetic acid), time 0 to 10 min, to 50:50 methanol(0.1% trifluoracetic acid)/water (0.1% trifluoracetic acid), time 10 min to 40 min, flow=10 ml/min (Rt= 36.8 min, un detection 254 nm) to yield 4.5 mgs (67%) 1-methyl-4-(2-carboxyethyl)-7-(5-guanidino-1-pentynyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione trifluoracetate. HRMS (FAB) molecular ion m/z=386.1823 (cald. C19H24N5O4, 386.1829). 1H NMR (D2O) 7.60 (1H, d, 4JHH, Ar--H o-CON), 7.51 (1H, dd, 4JHH =2 Hz, 3JHH =8 Hz, Ar--H p-CON), 7.20 (1H, d, 3JHH =8 Hz, Ar--H m-CON), 4.05 (1H, d, 2JHH =14 Hz, NCHHCO), 3.92 (1H, m, NCHHCH2), 3.72 (1H, d, 2JHH =14 Hz, NCHHCO), 3.40 (1H, m, NCHHCH2), 3.23-3.15 (5H, NCH3, H2NC(=NH2)NHCH2), 2.58 (2H, m, CH2CO2), 2.38 (2H, t, 3JHH=7 Hz, CHCCH2), 1.76 (2H, p, 3JHH =7 Hz, CH2CH2CH2).

Provenance & Evidence