Methyl 3-amino-2,2-dimethylpropanoate → methyl 3-[({3-[(6-cyano-1H-benzimidazol-1-yl)methyl]-1-hydroxycyclohexaneyl}methyl)amino]-2,2-dimethylpropanoate

Participants

Reaction Steps

A solution of 1-[(55)-1-oxaspiro[2.5]oct-5-ylmethyl]-1H-benzimidazole-6-carbonitrile (1.064 g, 3.98 mmol) and methyl 3-amino-2,2-dimethylpropanoate (0.679 g, 5.17 mmol) in isopropanol (13.27 mL) was stirred at 100° C. for 1 day. Reaction was concentrated and purified via silica gel chromatography (ISCO, 120 g silica gel column. Solvent A was DCM and solvent B was 0.1M NH3 in MeOH; 0-10% B over 15 min; 10% B over 6 min) to give methyl 3-[({3-[(6-cyano-1H-benzimidazol-1-yl)methyl]-1-hydroxycyclohexaneyl}methyl)amino]-2,2-dimethylpropanoate as a sticky solid (1.05 g, 66.1% yield). MS (m/z) 399.2 (M+H+).

Provenance & Evidence