Hydrochloric Acid → HCID 178495952, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of racemic trans 3-(6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentylamine (95.0 mg, 392 μmol), 2-bromoethyl methyl ether (59.9 mg, 431 μmol), potassium carbonate (108 mg, 780 μmol) and DMF (2 mL) was heated to 135° C. for 15 minutes using microwave irradiation. The mixture was filtered, concentrated in vacuo and purified by column chromatography on silica gel (gradient: DCM to 10% [2M NH3 in methanol] in DCM) followed by reverse phase HPLC (5 to 50% acetonitrile in water, +0.1% NH4OH). The colourless residue was treated with 1.25 M HCl in methanol (2 eq) in DCM and concentrated to afford 17.6 mg of racemic trans (2-methoxy-ethyl)-[3-(6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-amine hydrochloride was isolated as a beige gum. LCMS (Method A, ESI): RT=1.92 min, m+H=301.3; 1H NMR (400 MHz, DMSO) δ: 12.35 (s, 1H), 8.99 (s, 1H), 7.60 (t, 1H), 7.00 (dd, 1H), 5.65 (m, 1H), 3.59 (m, 1H), 3.47 (t, 2H), 3.28 (s, 3H), 2.83 (t, 2H), 2.47 (m, 2H, partially obscured by DMSO), 2.29-2.17 (m, 3H), 1.72 (m, 1H).

Provenance & Evidence