Dimethylamine → HCID 86613907, compound

Participants

Reaction Steps

To a solution of 6-(4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylic acid (0.14 g, 0.40 mol) in DMF was added BOP (0.515 g, 1.167 mmol) and the dimethylamine (2.0 M in THF) (0.035 g, 0.778 mmol). After 24 hours, the product mixture was concentrated under vacuum. The residual material was purified using reverse phase HPLC eluting with 5-95% acetonitrile (0.1% TFA) in H2O (0.1% TFA) to give 6-(4-fluorobenzyl)-4-methoxy-N,N, 2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide (ES MS M+1=388). A solution of this product (0.1 g, 0.3 mmol) in CH2Cl2 was treated with HBr (30 wt % in acetic acid) (0.104 g, 1.29 mmol) and after stirring at room temperature for 24 hours, concentrated under vacuum. The residual material was purified using reverse phase HPLC eluting with 5%-95% acetonitrile (0.1% TFA) in H2O (0.1% TFA) to afford the title compound.

Provenance & Evidence