1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Ammonium

Participants

Reaction Steps

To a suspension of 3(5-methylcarbamoyl-pyridin-2-yl)propionic acid hydrochloride (0.26 g, 1.06 mmol) in dichloromethane (20 mL) was added ethyldiisopropylamine (0.74 mL, 4.26 mmol), the solution was stirred for 5 min, and then 2-amino-N-(2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)-N-methylacetamide (0.5 g, 1.0 mmol) was added followed by HOBT (0.135 g, 1.0 mmol) and EDCI (0.28 mL, 1.59 mmol). The reaction mixture was then stirred overnight at room temperature and partitioned in dichloromethane (100 mL) and a saturated solution of NaHCO3 (100 mL). Organic layer was separated, dried (MgSO4) and concentrated to give oil, which was purified by flash chromatography using a mixture of dichloromethane- and a 5% ammonium solution in methanol (9:1) to give 6-(3-((2-((2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)amino)-3-oxopropyl)-N-methylnicotinamide as foam. LCMS (APCI) 690 (M+); 1HNMR (400 MHz, MeOD) δ 2.60 (t, 2H), 3.07 (s, 3H), 3.19 (t, 2H), 3.20 (s, 3H), 3.32-3.69 (dd, 2H), 4.01 (s, 3H), 5.19 (s, 2H), 5.46 (dd, 2H), 6.71-8.74 (m, 12H)

Provenance & Evidence