Dimethylamine → HCID 68505534, compound

Participants

Reaction Steps

A solution of 1 eq of 11-carboxy-14-cyclohexyl-3-fluoro-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocin-6-ium trifluoroacetate (prepared as described in Example 44, Step 1) in DCM (plus some drops of MeCN and DMF) (0.08 M) was added to a solution of 1.1 eq of 2-chloro-ethansulfonyl chloride in DCM (0.08 M) and 2.2 eq of Et3N and the mixture stirred at RT for 5 mins. At which time a solution of dimethylamine 2 M in THF (5 eq) was added and the mixture stirred at RT overnight. Volatiles were removed in vacuo. The crude was then purified by automated RP-MS-HPLC (stationary phase: column Waters SYMMETRY prep. C18, 7 μm, 19×300 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA). Fractions containing the pure compound were combined and freeze dried to afford the title compound as a white powder (16%).

Provenance & Evidence