1-iodo-3-isocyanatobenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 3-Iodophenylisocyanate (500 mg) was added to a solution of (5R)-3-{6-[2-{[(3-aminophenyl)methyl]oxy}ethoxy]hexyl}-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (700 mg) in dichloromethane (14 ml) and the mixture was stirred at 20° under nitrogen for 5 h. Isopropanol (14 ml) was added and the mixture was stirred for 16 h. The solvent was evaporated in vacuo to give a residue that was purified by Biotage. Elution with EtOAc-PE (2:1) gave the title compound (800 mg). LCMS RT=4.02 min, ES +ve 744 (MH)+. the mixture was stirred for 16 h The solvent was evaporated in vacuo to give a residue that was purified by Biotage Elution with EtOAc-PE (2:1)

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

Procedure: 3-Iodophenylisocyanate (500 mg) was added to a solution of (5R)-3-{6-[2-{[(3-aminophenyl)methyl]oxy}ethoxy]hexyl}-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (700 mg) in dichloromethane (14 ml) and the mixture was stirred at 20° under nitrogen for 5 h. Isopropanol (14 ml) was added and the mixture was stirred for 16 h. The solvent was evaporated in vacuo to give a residue that was purified by Biotage. Elution with EtOAc-PE (2:1) gave the title compound (800 mg). LCMS RT=4.02 min, ES +ve 744 (MH)+. the mixture was stirred for 16 h The solvent was evaporated in vacuo to give a residue that was purified by Biotage Elution with EtOAc-PE (2:1)

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

Procedure: To a dichloroethane solution (10 ml) of bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (540 mg), DMAP (12.2 mg) and 1-iodo-3-isocyanato-benzene (490 mg) were added, followed by refluxing for 17 hours. This was cooled to room temperature, and dichloromethane (40 ml) was added. After washing with saturated aqueous ammonium chloride solution (30 ml), the organic layer was dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off under reduced pressure, followed by silica gel column chromatography (hexane/dichloromethane/ethyl acetate=4/4/1 to 1/2/1), to obtain the desired compound as a crude product (404 mg, 51%). by refluxing for 17 hours After washing with saturated aqueous ammonium chloride solution (30 ml) the organic layer was dried over sodium sulfate After the sodium sulfate was filtered off the solvent was distilled off under reduced pressure

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

Procedure: 3-Iodophenylisocyanate (500 mg) was added to a solution of (5R)-3-{6-[2-{[(3-aminophenyl)methyl]oxy}ethoxy]hexyl}-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (700 mg) in dichloromethane (14 ml) and the mixture was stirred at 20° under nitrogen for 5 h. Isopropanol (14 ml) was added and the mixture was stirred for 16 h. The solvent was evaporated in vacuo to give a residue that was purified by Biotage. Elution with EtOAc-PE (2:1) gave the title compound (800 mg). LCMS RT=4.02 min, ES+ve 744 (MH)+. the mixture was stirred for 16 h The solvent was evaporated in vacuo to give a residue that was purified by Biotage Elution with EtOAc-PE (2:1)

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of ethyl carbazate (1.25 g) in dichloromethane (20 ml) was treated with 3-iodophenylisocyanate (1.7 g) at 0° C. The reaction mixture was allowed to warm to 20° C. and stirred for 2 h. Ethanol (2 ml) was added and the mixture was stirred for 0.5 h. The solvents were removed under reduced pressure and the residue was triturated in diethyl ether. The white solid was collected by filtration to give the title compound (2.4 g). LCMS RT=2.81 min the mixture was stirred for 0.5 h The solvents were removed under reduced pressure the residue was triturated in diethyl ether The white solid was collected by filtration

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of ethyl carbazate (1.25 g) in dichloromethane (20 ml) was treated with 3-iodophenylisocyanate (1.7 g) at 0° C. The reaction mixture was allowed to warm to 20° C. and stirred for 2 h. Ethanol (2 ml) was added and the mixture was stirred for 0.5 h. The solvents were removed under reduced pressure and the residue was triturated in diethyl ether. The white solid was collected by filtration to give the title compound (2.4 g). LCMS RT=2.81 min the mixture was stirred for 0.5 h The solvents were removed under reduced pressure the residue was triturated in diethyl ether The white solid was collected by filtration

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 3-iodophenylisocyanate (1.1 g) in DCM (10 ml) was treated with aminoacetaldehyde dimethyl acetal (0.49 ml) and stirred under nitrogen at 20° C. for 24 h. The reaction mixture was quenched by adding MeOH. The solvents were removed under reduced pressure to give the title compound (1.35 g) LCMS RT=2.92 min. The reaction mixture was quenched by adding MeOH The solvents were removed under reduced pressure

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

Procedure: A solution of 3-iodophenylisocyanate (0.1 g, 0.41 mmol) and morpholine (0.04 mL, 0.45 mmol) in 2 mL dioxane were heated at 100° C. overnight. The solvent was evaporated and the resulting product was used without purification. The solvent was evaporated the resulting product was used without purification

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

Procedure: 3-Iodophenylisocyanate (500 mg) was added to a solution of (5R)-3-{6-[2-{[(3-aminophenyl)methyl]oxy}ethoxy]hexyl}-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (700 mg) in dichloromethane (14 ml) and the mixture was stirred at 20° under nitrogen for 5 h. Isopropanol (14 ml) was added and the mixture was stirred for 16 h. The solvent was evaporated in vacuo to give a residue that was purified by Biotage. Elution with EtOAc-PE (2:1) gave the title compound (800 mg). LCMS RT=4.02 min, ES+ve 744 (MH)+. the mixture was stirred for 16 h The solvent was evaporated in vacuo to give a residue that was purified by Biotage Elution with EtOAc-PE (2:1)