Hydrochloric Acid → HCID 58997230, compound

Participants

Reaction Conditions

Reaction Steps

Hydroxylamine hydrochloride (1.0 g, 14.3 mmol) was dissolved in MeOH (6 mL) with slight heating. In a separate flask, KOH (1.36 g, 21.3 mmol) was dissolved in MeOH (6 mL) with heating to 60° C., then this was added to the above solution at 40° C. KCl precipitated out, and was cooled to 0° C. The clear portion of this suspension (3.2 mL) was added to (3-{[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-azetidin-1-yl)-acetic acid methyl ester (0.1411 g, 0.38 mmol) and stirred at room temperature for 24 hours. 1N HCl (3 mL) was added until neutral, and extracted with CH2Cl2 (3×40 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated. Purification of the crude material by column chromatography on silica gel (25:1:1 then 10:1:1 CH2Cl2-MeOH—NH4OH) provided 67.3 mg (48%) of COMPOUND 346 as a white solid. 1H NMR (CDCl3) δ 2.07 (s, 6H), 2.57-2.73 (m, 5H), 3.03 (s, 2H), 3.32 (t, 2H, J=6.0 Hz), 3.69 (s, 4H), 7.09-7.13 (m, 2H), 7.40 (d, 2H, J=7.5 Hz), 8.36 (d, 2H, J=3.9 Hz). 13C NMR (CDCl3) δ 18.23, 29.15, 58.56, 59.63, 60.28, 60.69, 123.06, 133.80, 138.65, 146.22, 156.94, 167.02. ES-MS m/z 370.5 (M+H). Anal. Calcd. for C20H27N5O2.0.6CH4O.0.5H2O: C, 62.21; H, 7.70; N, 17.61. Found: C, 62.06; H, 7.61; N, 17.49.

Provenance & Evidence