Dimethylformamide → HCID 18332660, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 336 mg of 2-methanesulfonyl-4-[benzimidazol-1-yl]pyrimidine (EXAMPLE 1) in 2 mL of DMF was added a solution of 273 mg of 1-benzyloxycarbonyl-3-aminomethylpyrrolidine in 2 mL of toluene. The mixture was heated to 100° C. and stirred at this temperature for 18 h, then cooled, diluted with 20 mL of EtOAc, and washed with 2×10 mL of water and 10 ml of brine. The organic phase was dried over MgSO4 and concentrated. The residue was purified by flash chromatography, eluting with a gradient system of 4:1 hexanes-acetone to 2:1 hexanes-acetone, to yield 338 mg of the title compound as an off-white foam. 1H NMR (500 MHz, CDCl3): δ 8.61 (s, 1H), 8.38 (d, J=5.0 Hz, 1H) 8.16 (br t, J=7.1 Hz, 1H), 7.86 (d, J=8.2 Hz, 1H), 7.27-7.42 (m, 5H), 6.81 (d, J=5.5 Hz, 1H), 5.55 (br s, 1H), 5.06-5.19(m, 2H), 3.50-3.75 (m, 4H), 3.38-3.50 (m, 1H), 3.25 (ddd, J=6.9, 10.8, 17.6 Hz, 1H), 2.58-2.70 (m, 1H), 2.06-2.16 (m, 1H), 1.68-1.82 (m, 1H). Mass spectrum (ESI) 429.2 (M+1).

Provenance & Evidence