Skip to main content
. Author manuscript; available in PMC: 2008 Oct 18.
Published in final edited form as: J Med Chem. 2007 Sep 26;50(21):5217–5226. doi: 10.1021/jm070705c

Scheme 4.

Scheme 4

Syntheses of 1-adamantyl-3-substituted alkyl-ureas with a sulfonamide (20 and 21) and of amide derivatives (22 and 23) of compound 15: (a) 2-aminoethoxyethanol (for compound 20) or 5-amino-1-pentanol (for compound 21), methanesulfonic anhydride, acetonitrile, rt, (b) I, NaH, DMF, rt, (c) diethylene glycol monoethyl ether, NaH, DMF, rt, (d) 1N NaOH, ethanol, rt, (e) 1-adamantylamine, EDCI, DMAP, dichloromethane, rt, (f) di-(tert-butyl) dicarbonate, dioxane, rt, (g) 2-(ethoxyethoxy)ethyl bromide (prepared as described in Scheme 2 (B); II), NaH, DMF, rt, (h) (1) 4N HCl in dioxane, rt, (2) 1-adamantylacetic acid, triethylamine, EDCI, DMAP, dichloromethane, rt.