Hydrochloric Acid → HCID 178513998, compound

Participants

Reaction Steps

In the same fashion as for Compound III, (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide and 4-(4-Formyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester were reacted to produce an initial tert-butyl carbamate condensation product. This material was treated with 4N hydrochloric acid in dioxane at 40° C. overnight. Concentration followed by reverse phase chromatography on a Gilson chromatograph afforded fractions which were lyophilized to afford the title compound (43%). 1H NMR (d6-DMSO): 13.19 (br s, 1H), 8.77 (m, 2H), 8.04 (s, 1H), 8.02 (s, 1H), 7.95 (s, 1H), 7.78 (s, 1H), 7.13-7.45 (m, 4H), 6.38 (m, 2H), 5.17 (t, J=8 Hz, 1H), 3.49 (m, 4H), 3.26 (m, 4H), 2.91 (s, 1H), 2.80 (s, 1H), 2.62 (d, J=8 Hz, 1H), 2.23 (d, J=9 Hz, 1H), 1.40 (d, J=9 Hz, 1H). MS: 465.09 (M+H). HPLC retention time: 1.79 minutes (G Method).

Provenance & Evidence