Trifluoroacetic acid → HCID 21462996, compound

Participants

Reaction Steps

A solution of (E)-1-tert-butyloxycarbonyl-3-(4-[2-(5-methylfuran-2-yl)ethenyl]-1,2,3,6-tetrahydropyridin-1-yl)methylpyrrolo[2,3-b]pyridine (160 mg, 0.38 mmol) in anhydrous dichloromethane (5 ml) was treated with trifluoroacetic acid (500 ml, 6.5 mmol) and stirred at room temperature for two hours. Ammonium hydroxide solution (5 ml) was added and the whole mixture evaporated in vacuo. The residue was azeotroped with toluene. The crude material was chromatographed on silica gel with 5% methanol in dichloromethane as eluant to afford the title compound as a pale lemon solid (70 mg, 57%), m.p. 180° C. (dec.); (Found: C, 71.47; H, 6.46; N, 12.01. C20 H21N3O.H2O requires C, 71.19; H, 6.87; N, 12.42%); δH (DMSO-d6) 2.15-2.30 (5H, m, tetrahydropyridinyl CH2 and ArCH3), 2.59 (2H, t, J 5.5 Hz, tetrahydropyridinyl CH2), 3.02-3.10 (2H, m, tetrahydropyridinyl CH2), 3.71 (2H, s, NCH2Ar), 5.78-5.86 (1H, m, tetrahydropyridinyl 5-H), 6.05-6.10 (1H, m, furan 4-H), 6.16-6.30 (2H, m, CH=CHAr and furan 3-H), 6.55 (1H, d, J 16.1 Hz, CH=CHAr), 7.02 (1H, dd, J 7.8, 4.8 Hz, 5-H), 7.34-7.38 (1H, m, 2-H), 8.01 (1H, d, J 7.8 Hz, 4-H), 8.18 (1H, d, J 4.6 Hz, 6-H), and 11.45 (1H, s, NH); m/z (CI+, NH3) 320 (M+1)+.

Provenance & Evidence