反应详情

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).

1. concentrationThe reaction mixture was concentrated in vacuo
2. dissolutionredissolved in DMF (10 mL)
3. concentrationThe solution was concentrated in vacuo
4. dissolutionredissolved in CH2Cl2 (20 mL)
5. customThe reaction mixture was quenched with a solution of saturated NaHCO3 (20 mL)
6. extractionExtract with CH2Cl2 (3×25 mL)
7. dry with materialThe combined organic extracts were dried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto afford a light yellow oil
11. customPurification via column chromatography on silica gel (CH2Cl2