Sodium Iodide → HCID 54720512, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(3-chloro-4-fluorobenzyl)-3,4-dihydroxy-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide (0.075 g, 0.19 mmol; Example 13, step 5) and magnesium methoxide in methanol (0.06 mL, 6-10% methanol solution available from Aldrich) in DMSO (2 mL) was heated at 60° C. for 30 minutes. Methanol was exhaustively removed under vacuum over 45 minutes. The residual DMSO solution was treated with 1-bromo-2-chloroethane (0.136 g, 0.95 mmol) and stirred at 60° C. under an atmosphere of nitrogen overnight. The product mixture was treated with pyrrolidine (0.27 g, 3.8 mmol) and sodium iodide (0.14 g, 0.95 mmol) and heated at 60° C. overnight. The reaction was partitioned between methylene chloride and aqueous sodium bisulfate. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to preparative HPLC purification on C-18 reverse stationary phase column eluting with a gradient of water—acetonitrile in the presence of 0.1% trifluoroacetic acid. Collection and lyophilization of appropriate fractions provided the titled compound.

Provenance & Evidence