2-amino-4-bromo-N-methylbenzamide

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.5 ml of triethyl orthopropionate and 30 μL of acetic acid were added to 1 ml solution of N-methyl-2-pyrolidine with 796 mg of N-methyl-2-amino4-bromobenzamide, and the mixture was stirred at 100° C. for 1 hour. Saturated sodium bicarbonate aqueous solution was added to the reaction solution, and extracted with ether. Ether layer was washed with saturated saline solution, and dried with anhydrous magnesium sulfate. After distilling out the solvents under reduced pressure, the residues were separated and purified by silicagel column chromatography (hexane/ethyl acetate=4/1), to obtain 653 mg of the above compound as a colorless solid. extracted with ether Ether layer was washed with saturated saline solution dried with anhydrous magnesium sulfate After distilling out the solvents under reduced pressure the residues were separated purified by silicagel column chromatography (hexane/ethyl acetate=4/1)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.5 ml of triethyl orthopropionate and 30 μL of acetic acid were added to 1 ml solution of N-methyl-2-pyrolidine with 796 mg of N-methyl-2-amino4-bromobenzamide, and the mixture was stirred at 100° C. for 1 hour. Saturated sodium bicarbonate aqueous solution was added to the reaction solution, and extracted with ether. Ether layer was washed with saturated saline solution, and dried with anhydrous magnesium sulfate. After distilling out the solvents under reduced pressure, the residues were separated and purified by silicagel column chromatography (hexane/ethyl acetate=4/1), to obtain 653 mg of the above compound as a colorless solid. extracted with ether Ether layer was washed with saturated saline solution dried with anhydrous magnesium sulfate After distilling out the solvents under reduced pressure the residues were separated purified by silicagel column chromatography (hexane/ethyl acetate=4/1)

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

Procedure: 30 ml of 2.0 M methylamine-methanol solution was added to 6.28 mg of 7-bromo-1H-benzo[1,3]oxazine-2,4-dion, and the mixture was stirred at room temperature for 2 hours. The reaction solution was distilled outunder reduced pressure, to obtain 6.57 mg of the above compound. The reaction solution was distilled outunder reduced pressure

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

Procedure: 30 ml of 2.0 M methylamine-methanol solution was added to 6.28 mg of 7-bromo-1H-benzo[1,3]oxazine-2,4-dion, and the mixture was stirred at room temperature for 2 hours. The reaction solution was distilled outunder reduced pressure, to obtain 6.57 mg of the above compound. The reaction solution was distilled outunder reduced pressure

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

Procedure: To a mixture of 3-methoxypropanoic acid (0.25 mL, 2.62 mmol), DMAP (0.64 g, 5.24 mmol) and dry DCM (5 mL) was added methanesulfonyl chloride (0.22 mL, 2.88 mmol) dropwise at 0° C. under nitrogen atmosphere. 2-Amino-4-bromo-N-methylbenzamide (0.3 g, 1.31 mmol) was added after stirring for 1 h, and the temperature was allowed to rise to room temperature slowly. The reaction mixture was quenched with sat. NH4Cl solution after 3 h and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with NaHCO3, dried over Na2SO4, filtered, and evaporated to give 0.39 g of the target compound. MS (ESI): 315, 317 (MH+). to rise to room temperature The reaction mixture was quenched with sat. NH4Cl solution after 3 h extracted with ethyl acetate (3×10 mL) The combined organic layers were washed with NaHCO3 dried over Na2SO4 filtered evaporated

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

Procedure: To a mixture of 2-amino-4-bromobenzoic acid (5.0 g, 23.1 mmol) and dioxane (50 mL) was added triphosgene (2.3 g, 7.75 mmol). The reaction mixture was heated to reflux and stirred for 4 h. Methylamine (40% in water, 2 mL, 23.1 mmol) was added dropwise after the mixture was cooled to room temperature. After stirring for 30 min, the solution was evaporated under reduced pressure and the residue was redissolved in DCM which was washed with sat. NaHCO3 aqueous solution, dried over Na2SO4, filtered, and evaporated to give 4.6 g of the target compound. MS (ESI): 229, 231 (MH+). The reaction mixture was heated to reflux After stirring for 30 min the solution was evaporated under reduced pressure the residue was redissolved in DCM which was washed with sat. NaHCO3 aqueous solution dried over Na2SO4 filtered evaporated

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.5 ml of triethyl orthopropionate and 30 μL of acetic acid were added to 1 ml solution of N-methyl-2-pyrolidine with 796 mg of N-methyl-2-amino4-bromobenzamide, and the mixture was stirred at 100° C. for 1 hour. Saturated sodium bicarbonate aqueous solution was added to the reaction solution, and extracted with ether. Ether layer was washed with saturated saline solution, and dried with anhydrous magnesium sulfate. After distilling out the solvents under reduced pressure, the residues were separated and purified by silicagel column chromatography (hexane/ethyl acetate=4/1), to obtain 653 mg of the above compound as a colorless solid. extracted with ether Ether layer was washed with saturated saline solution dried with anhydrous magnesium sulfate After distilling out the solvents under reduced pressure the residues were separated purified by silicagel column chromatography (hexane/ethyl acetate=4/1)

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

Procedure: 30 ml of 2.0 M methylamine-methanol solution was added to 6.28 mg of 7-bromo-1H-benzo[1,3]oxazine-2,4-dion, and the mixture was stirred at room temperature for 2 hours. The reaction solution was distilled outunder reduced pressure, to obtain 6.57 mg of the above compound. The reaction solution was distilled outunder reduced pressure