Nitrogen → 1-(4-{[(3,5-dimethyl-pyridin-2-ylmethyl)-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-3-hydroxymethyl-benzyl)-3-(1H-imidazol-2-yl)-urea

Participants

Reaction Steps

To a solution of 1,1-carbonyldiimidazole (117 mg, 0.72 mmol) dissolved in CH2Cl2 (10 mL) add 2-aminoimidazole sulfate (95 mg, 0.72 mmol). The solution was stirred for 16 hours under a positive pressure of N2. The reaction mixture was concentrated in vacuo and redissolved in DMF (10 mL). Addition of DIPEA (250 ul, 1.44 mmol) and (5-aminoethyl-2-{[(3,5-dimethyl-pyridin-2-ylmethyl)-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-phenyl)-methanol (100 mg, 0.24 mmol) was made to the solution. The solution was stirred at 75° C. for 16 hours under a positive pressure of N2. The solution was concentrated in vacuo and redissolved in CH2Cl2 (20 mL). The reaction mixture was quenched with a solution of saturated NaHCO3 (20 mL). Extract with CH2Cl2 (3×25 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to afford a light yellow oil. Purification via column chromatography on silica gel (CH2Cl2:MeOH, 97:3, v/v) afforded the product as a colorless oil (20 mg, 16%). 1H NMR (CDCl3) δ 1.55 (m, 1H), 2.05 (m, 3H), 2.18 (s, 3H), 2.24 (s, 3H), 2.77 (m, 2H), 3.61 (m, 1H), 3.67 (d, 1H, J=11.4 Hz), 3.72 (d, 1H, J=12.7 Hz), 3.83 (m, 1H), 4.11 (m, 2H), 4.35 (m, 3H), 6.59 (s, 2H), 7.23 (m, 5H), 7.66 (s, 1H), 8.16 (s, 1H), 8.31 (m, 1H). ES-MS m/z 526 (M+H).

Provenance & Evidence