Diisopropylethylamine → HCID 21106443, compound

Participants

Reaction Steps

4-(3-Phenylamino-[1,2,4]triazol-1-yl)-pyridin-2-ylamine (50 mg, 0.20 mMol) was dissolved in 2.5 mL of NMP with (50 μL, 67.4 mg, 0.52 mMol) of Hunig's base and (30 μL, 32 mg, 0.2 mMol) of cyclopentylmethyl carbonyl chloride. The reaction was stirred at ambient temperature for 18 hr. LC shows starting material, mono acylated material, and a majority of the bis acylated imide. Another alliquot of the acylating agent was added and the reaction was stirred until all starting material was consumed. Five drops of 2.0N sodium hydroxide was then added and the reaction was stirred for ten hours at ambient temperature, until all of the imide was hydrolyzed. The reaction mixture was acidified with TFA and the crude material was purified via HPLC, C18 silica with a gradient of acetonitrile/water/0.1% TFA as the eluent. Yield˜13 mg of a pale yellow powder as the TFA salt; (18%). 1H NMR 500 MHz (DMSO-d6) ∂ 1.29m, 2H), 1.5(m, 2H), 1.77(m, 2H), 2.25(m, 1H), 2.4(d, 2H), 6.88(t, 1H), 7.28(t, 2H), 7.53(d, 1H), 7.63(d, 2H), 8.35(d, 1H), 8.55(d, 1H), 9.2(s, 1H), 9.57(s, 1H), 10.6(s ex, 1H). LC/MS [M+H+] 363

Provenance & Evidence