Modulators of cellular adhesion
An aliphatic, compound technology, used in organic chemistry, organic active ingredients, medical preparations containing active ingredients, etc.
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Embodiment 1
[0405] This example describes the synthesis of the following compounds
[0406]
[0407] It was prepared according to Scheme 1A and the following procedure.
[0408] Diagram 1A
[0409]
[0410] a) A solution of 3-methoxyphenylethylamine (0.2 mol) and formaldehyde (0.22 mol) in aqueous HCl (20%, 500 mL) was heated at 80°C for 4 hours. The reaction was then concentrated to dryness, and the residue was dissolved in hydrobromic acid (40% in water, 500 mL) and refluxed for 24 hours. The reaction was concentrated to give a brown solid which was used without purification. Water (200 mL) and tetrahydrofuran ("THF") (300 mL) were added to the residue and sodium carbonate (solid, 0.5 mol) was added very carefully to the resulting mixture, followed by di-tert-butyl dicarbonate (0.3 mol) . After 15 hours at room temperature, the reaction was extracted with ethyl acetate (1 L), and the organic extract was washed with saturated potassium dihydrogen phosphate and brine, dried over...
Embodiment 2
[0427] This example describes the synthesis of the following compounds,
[0428]
[0429] It was prepared according to the procedure of Example 1g except that 4-chlorobenzoic acid was used instead of compound 1.11. 1 H NMR (400MHz, CD 3 OD): δ7.64(m, 2H), 7.35-7.49(m, 5H), 7.11(s, 1H), 4.98(t, J=8.0Hz, 1H), 4.63 and .88(m, 2H), 3.83 (d, J = 8.0 Hz, 2H), 3.68 and 3.98 (m, 2H), 2.89 (m, 2H) ppm; ESI-MS (m / z): (M+1) 579.90.
Embodiment 3
[0431] This example describes the synthesis of the following compounds,
[0432]
[0433] It was prepared according to Scheme 2 and the following procedure.
[0434] Diagram 2
[0435]
[0436] a) To 10 mmol of commercially available 3.1 in 20 mL of MeOH and 20 mL of CH at 0 °C 2 Cl 2 Slowly add 20 mmol of 2.0M TMSCHN in hexane to the solution in 2 , and the resulting mixture was stirred at room temperature for 30 minutes. The solvent was removed and the residue was dried in vacuo to give crude 3.2.
[0437] b) Then, compound 3.2 and 15 mmol of isopropyl azide in 0.2 mmol of CuI, 0.2 mmol of Et 3 In the presence of N in 50 mL of CH 3 CN was stirred overnight at room temperature. The solvent was removed and the residue was purified by column chromatography to give compound 3.3 in 55% yield. ESI-MS (m / z): (M+1) 313.20.
[0438] c) A mixture of 2 mmol of compound 3.3 in 10 mL of 4.0N HCl in dioxane was stirred at room temperature for 12 hours. The solvent was remo...
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