tert-butyl N-(2-amino-4-methoxyphenyl)carbamate

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: 10% Palladium on carbon (120 mg) was added to a solution of 4-methoxy-2-nitrophenylcarbamic acid t-butyl ester (Reference Compound No. 11-1, 1.3 g, 4.8 mmol) in methanol (20 mL), and then the reaction mixture was stirred under a hydrogen atmosphere at room temperature for 9 hours. The insoluble was filtered off, and then the solvent was evaporated under reduced pressure. The resulting solid was collected by filtration with hexane to give 1.1 g of the title reference compound as a pale brown solid quantitatively. The insoluble was filtered off the solvent was evaporated under reduced pressure The resulting solid was collected by filtration with hexane to give 1.1 g of the title reference compound as a pale brown solid quantitatively

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

Procedure: The title compound was prepared from (2-amino-4-methoxy-phenyl)-carbamic acid tert-butyl ester (Example J9) and 3-oxo-3-(3-pyridin-4-yl-phenyl)-propionic acid tert-butyl ester (Example K2) according to the general procedure M. Obtained as a light yellow solid (258 mg).

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

Procedure: The title compound was prepared from (2-amino-4-methoxy-phenyl)-carbamic acid tert-butyl ester (Example J9) and 3-oxo-3-(3-pyridin-4-yl-phenyl)-propionic acid tert-butyl ester (Example K2) according to the general procedure M. Obtained as a light yellow solid (258 mg).

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

Procedure: The title compound was prepared from (4-methoxy-2-nitro-phenyl)-carbamic acid tert-butyl ester (Example A10) by hydrogenation with 10% Pd/C according to the general procedure J (method a). Obtained as a white solid (19.377 g).

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

Procedure: The title compound was prepared from (4-methoxy-2-nitro-phenyl)-carbamic acid tert-butyl ester (Example A10) by hydrogenation with 10% Pd/C according to the general procedure J (method a). Obtained as a white solid (19.377 g).

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

Procedure: A suspension of 5-[(Z)-(methylthio)(phenylimino)methyl]-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylic acid obtained from step III of example 116 (1 eq), (2-amino-4-methoxy-phenyl)-carbamic acid tert-butyl ester (1.2 eq), EDCI (1.2 eq), HOBt (1.2 eq) and triethylamine in DMF were stirred at room temperature for 15 h. Solvent was evaporated and the residue was purified by either column chromatography or preparative HPLC to afford methyl 2-({2-[(tert-butoxycarbonyl)amino]-4-methoxyphenyl}carbamoyl)-N-phenyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-5(4H)-carbimidothioate. Solvent was evaporated the residue was purified by either column chromatography or preparative HPLC

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Intermediate 36 (7.3 g, 30.6 mmol) was dissolved in DMF (70 mL). To this solution was added anhydrous K2CO3 (4.7 g, 33.7 mmol) and the mixture was heated to reflux (130° C.) for 5 h. The solvent was removed under pressure, the residue was poured into ice water, and the aq phase was extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SO4, concentrated under vacuum, and the resulting yellow solid was recrystallized from EtOH to give 5-methoxy-1H-benzo[d]imidazol-2(3H)-one (intermediate 37) (3.6 g, 72%) as a yellow solid. mp: 249-251° C. the mixture was heated The solvent was removed under pressure the residue was poured into ice water the aq phase was extracted with EtOAc The combined organic layers were dried over anhydrous Na2SO4 concentrated under vacuum the resulting yellow solid was recrystallized from EtOH

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

Procedure: 10% Palladium on carbon (120 mg) was added to a solution of 4-methoxy-2-nitrophenylcarbamic acid t-butyl ester (Reference Compound No. 11-1, 1.3 g, 4.8 mmol) in methanol (20 mL), and then the reaction mixture was stirred under a hydrogen atmosphere at room temperature for 9 hours. The insoluble was filtered off, and then the solvent was evaporated under reduced pressure. The resulting solid was collected by filtration with hexane to give 1.1 g of the title reference compound as a pale brown solid quantitatively. The insoluble was filtered off the solvent was evaporated under reduced pressure The resulting solid was collected by filtration with hexane to give 1.1 g of the title reference compound as a pale brown solid quantitatively

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

Procedure: The title compound was prepared from (2-amino-4-methoxy-phenyl)-carbamic acid tert-butyl ester (Example J9) and 3-oxo-3-(3-pyridin-4-yl-phenyl)-propionic acid tert-butyl ester (Example K2) according to the general procedure M. Obtained as a light yellow solid (258 mg).