1,2,3,4-Tetrahydroisoquinoline → HCID 18332646, compound

Participants

Reaction Steps

To a solution of 2-[1-(1-(4-nitrophenyl)oxycarbonylpiperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine (14.5 mg, 0.03 mmol) in CH2Cl2 (0.5 mL) was added 1,2,3,4-tetrahydroisoquinoline (4.3 gL, 0.033 mmol) followed by a few crystals of dimethylaminopyridine. The reaction mixture was stirred for 4 days, the solvent was removed under reduced pressure, and the crude material was purified by preparative thin layer chromatography eluting with 1:1 acetone:hexane to obtain 4 mg of the title compound. Partial 1H NMR (500 MHz, CDCl3): δ 8.61 (s, 1H); 8.37 (br s, 1H); 8.16 (d, J=7.3 Hz, 1H); 7.86 (d, J=7.3 Hz, 1H); 7.39 m, 2H); 7.15-7.04 (aromatic H's, 4H); 6.78 (d, J=5.5 Hz, 1H); 4.4 (s, 2H); 1.31 (d, J=6.6 Hz, 3H). Mass spectrum 482.4 (LC-MS, M+1).

Provenance & Evidence