Hydrochloric Acid → HCID 58459131, compound

Participants

Reaction Steps

A stirred solution of (S)-methyl 3-(2-(tert-butoxycarbonylamino)propanamido)-2-(cyclopropylamino)benzoate (600 mg, 1.6 mmol) in HOAc (20 mL) was heated at 60° C. for 1.5 h, and cooled to rt. After concentration of the mixture in vacuo, the residue was subjected to 4M HCl in dioxane (10 mL), and stirred at rt for 40 min. The mixture was concentrated in vacuo, dissolved in water (5 mL) and basified with 1N NaOH to pH 9.5. The mixture was concentrated and MeOH-DCM (1:1) was added to the residue to get the desired product into solution. The solution was concentrated in vacuo and the residue was purified by column chromatography on a silica gel column using DCM-MeOH—NH4OH (9:1:0.05) as eluent to give (S)-methyl 2-(1-aminoethyl)-1-cyclopropyl-1H-benzo[d]imidazole-7-carboxylate: 1H NMR (400 MHz, CDCl3) δ 7.86 (1H, d, J=8.0 Hz), 7.63 (1H, d, J=8.0 Hz), 7.27 (1H, t, J=8.0 Hz), 4.62 (1H, q, J=8.0 Hz), 4.01 (3H, s), 3.58-3.50 (3H, m), 1.65 (3H, d, J=8.0 Hz), 1.22-1.06 (2H, m), 0.95-0.65 (2H, m); LC-MS (ESI) m/z 260.0 [M+H]+.

Provenance & Evidence