Triethylphosphine → HCID 66926083, compound

Participants

Reaction Steps

(+/−)-Ethanesulfonyl-trans-4-methyl-piperidine-3-carboxylic acid N′-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-hydrazide (107 mg, 0.22 mmol) was cyclized to triazolo-tricyclic product using similar conditions to those described in example 17 above [however, after over-night stirring an extra 4 equivalents of N,N-diisopropylethylamine and an extra 3 equivalents of triethylphosphine were added and the mixture was stirred an extra 6 hours before work up]. The crude product was purified by preparative TLC, eluting with 90% ethyl acetate in hexanes. The impure product was collected and purified again by preparative TLC eluting first with 3.75% methanol in methylene chloride and then a second time with 5% methanol in methylene chloride. The product band was collected to afford 41 mg of (+/−)-1-(1-ethanesulfonyl-trans-4-methyl-piperidin-3-yl)-6-(2-trimethylsilanyl-ethoxymethyl)-6H-2,3,5,6,8b-pentaaza-as-indacene as a light yellow-white powder. MS (M+H)+=479.

Provenance & Evidence