3-methoxy-4-phenylaniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The titled compound was prepared from the product of Step 5 and 1-amino-3-methoxy-4-phenylbenzene using the procedure described in Step 3 of Example 1.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The titled compound was prepared from the product of Step 5 and 1-amino-3-methoxy-4-phenylbenzene using the procedure described in Step 3 of Example 1.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound is prepared by the general method exemplified in Example 1 using 3-(4-hexanoyl-benzoylamino)-propionic acid methyl ester (Preparation 5) and 2-methoxy-biphenyl-4-ylamine as starting materials. MS (ES): 475.2 [M+H]+.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8 g of the product obtained in Stage B is dissolved at 40° C. in 60 ml of glacial acetic acid. Then a solution of 5 ml of concentrated sulphuric acid in 80 ml of water is added. The reaction medium is cooled down to 0° C. Then a solution of 2.77 g of sodium nitrite in 35 ml of water is added dropwise over one hour. Agitation is carried out for one hour at 0° C., and a solution of 13.33 g of potassium iodide, in 25 ml of water is added dropwise. The suspension obtained is maintained at 0° C. for one hour, brought to 10° C. over 40 minutes, maintained at 10° C. for one hour, and brought to 20° C. over 30 minutes. It is poured into water, and extraction is carried out with ethyl acetate. The organic phases are collected and washed (aqueous solution of NaHSO3 then NaHCO3). They are dried and evaporated under reduced pressure. The product obtained is chromatographed, eluting with a heptane-methylene chloride mixture (9-1) and 9.6 g of sought product is obtained, melting at 57° C. The suspension obtained is maintained at 0° C. for one hour brought to 10° C. over 40 minutes maintained at 10° C. for one hour brought to 20° C. over 30 minutes The organic phases are collected washed (aqueous solution of NaHSO3 They are dried evaporated under reduced pressure The product obtained is chromatographed eluting with a heptane-methylene chloride mixture (9-1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.6 g of 10% by weight of palladium on charcoal is added to a solution of 11.2 g of the product obtained in Stage A in 150 ml of ethyl acetate. The suspension obtained is agitated under 1.3 atmospheres of hydrogen. After the absorption of hydrogen has stopped, the reaction medium is returned to normal atmospheric pressure, followed by filtration and evaporation under reduced pressure in order to obtain 9.64 g of sought product melting at 56° C. The suspension obtained After the absorption of hydrogen followed by filtration and evaporation under reduced pressure in order

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-amino-3-methoxy-4-phenylbenzene in 1,2-dichloroethane at 0° C. was added 4A powdered molecular sieves and sodium triacetoxyborohydride. 1-(4-Cyanobenzyl)-5-imidazole-carboxaldehyde was added, followed by 5 drops of acetic acid. The cooling bath was removed after 5 hours, and the reaction was stirred for another 15 hours. The reaction was poured into ethyl acetate and water. The organic layer was extracted with sat. aq. NaHCO3 solution and brine, then dried (Na2SO4) and concentrated in vacuo to provide the product. The cooling bath was removed after 5 hours The reaction was poured into ethyl acetate and water The organic layer was extracted with sat. aq. NaHCO3 solution and brine dried (Na2SO4) concentrated in vacuo to provide the product

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The titled compound was prepared from the product of Step 5 and 1-amino-3-methoxy-4-phenylbenzene using the procedure described in Step 3 of Example 1.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound is prepared by the general method exemplified in Example 1 using 3-(4-hexanoyl-benzoylamino)-propionic acid methyl ester (Preparation 5) and 2-methoxy-biphenyl-4-ylamine as starting materials. MS (ES): 475.2 [M+H]+.