1,3-Propanediamine → HCID 178465186, compound

Participants

Reaction Steps

A solution of 1-[2-chloro6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-1-deoxy-N-ethyl-β-D-ribofuranuronamide (0.310, 0.592 mmol) in dimethylsulphoxide (2 ml) was heated with 1,3-diaminopropane (0.542 g, 7.31 mmol) at 120° for 24h. The cooled mixture was partitioned between ethyl acetate (50 ml) and water (50 ml) and the aqueous phase was separated and extracted with ethyl acetate (20 ml). The combined ethyl acetate solution was washed with water (20 ml), dried (MgSO4) and evaporated to leave a froth (0.302 g). This froth (0.3 g) was dissolved in 50% aqueous methanol (20 ml) and the solution was heated at reflux with pyrazole-1-carboxamidine hydrochloride (0.099 g, 0.675 mmol) and imidazole (0.05 g, 0.734 mmol) for 18h. More pyrazole-1-carboxamidine hydrochloride (0.099 g, 0.675 mmol) was added and heating was continued for a further 24h. The mixture was evaporated to leave a solid which was purified by preparative HPLC (20-60% acetonitrile) to give the title compound (0.202 g) as a solid from ether. The product had MH+ =603, nmr(δ,DMSO-d6) includes 1.02(t,3H), 1.7-1.9(m,2H), 3.05-3.25(m,4H), 3.3-3.5(m,2H), 4.15-4.25(m,1H), 4.8(s,1H), 4.5-4.7(m,2H), 5.85(d,1H), 7.15-7.4(m,10H), 7.5-7.65(m,1H), 8.12(s,1H), 8.1-8.25(m,1H).

Provenance & Evidence