Diisopropylethylamine → HCID 23591838, compound

Participants

Reaction Steps

The amine (1.5–2.0 equivalents) is added to a stirred solution of acid 4 (1.0 eq., 25 mg), HBTU (1.5 eq.), Hünig's base (2.0 eq.) and DMF (0.4 ml). The acid 4 is pre-activated by premixed the acid 4, HBTU, Hünig's base and DMF together sequentially in this order in a vial at room temperature under argon. The reaction is stirred for 3–4 h until complete as shown by LCMS and HPLC. At times, it is necessary to add 0.25 or 0.5 equivalents more of the coupling reagents to complete the reaction. The reaction is purified by preparative HPLC. The entire reaction is injected directly onto the preparative HPLC. The purified fractions are pooled and lyophilized to give the amide 5 as a yellow powder in greater than 85% purity and in yields of 50–70%. Preparation of N-(2-{[3-(2,4-dichlorophenyl)-4-cyanophenyl]amino}ethyl)(tert-butoxy)carboxamide (6).

Provenance & Evidence