Methods for the preparation of hiv attachment inhibitor piperazine prodrug compound

A method of making the compound

• which comprises:
• (a) acylating the compound 10
• using
• to yield the compound 11
• and then
• (b) reacting compound 11 with compound 13
• in an activation reaction to produce compound 14
• and
• (c) adding the triazolyl compound 9
• in the presence of Cu ion and a ligand to obtain compound 15
• and
• (d) reacting compound 17
• with compound 15 to produce compound 18
• and
• (e) conducting a functional group interconversion reaction to yield Compound II above;
• wherein:
• R5═—H, —OR, —NR2, —Cl, —Br, —I, —SR;
• R6═—H, -Boc, -Piv, —SO2Aryl, —CH2SAryl, —CH2OP(O)(OR)2, —CH2OR, —CH2Aryl, —Li, Na, K, Ca, Mg, TMG;
• R=each independently —H, —C1-C6 alkyl, -aryl, —CH2Aryl;
• X1═—H, —Cl, —Br, —I,
• X5═—H, —OR, —NR2—Cl, —Br, —I, —SR;
• X6═—H, —OR, —NR2, —Cl, —Br, —I, —SR, —SO2R, —SR2+, —OSO2R, —OSO3R;
• and X7═—Cl, —Br, —I, —OSO2R.