2-amino-5-bromobenzenesulfonamide

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:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 2-amino-5-bromobenzenesulfonamide (0.8 g; 3.2 mmol) and potassium carbonate (0.54 g; 3.9 mmol) in acetone (20 ml) was added isopropyl isothiocyanate (0.387 g; 3.84 mmol). The mixture was heated to 60° C. and after 16 hr cooled, concentrated in vacuo and the crude residue was taken up in tetrahydrofuran (50 ml) and cooled to 0° C. To the cooled mixture was added triethylamine (0.648 g; 6.4 mmol) followed by the addition of phosgene in toluene 1.9M (1.82 ml) over 2 min. After 1 hr at 0° C. the mixture was concentrated in vacuo. The crude product was taken up in water (10 ml) and pH was adjusted to 6 with sodium bicarbonate. The precipitated product was collected by filtration and dried in vacuo at 50° C. for 16 hr giving 390 mg (38.3%) of the title compound; m.p. >220° C. cooled concentrated in vacuo cooled to 0° C After 1 hr at 0° C. the mixture was concentrated in vacuo The precipitated product was collected by filtration dried in vacuo at 50° C. for 16 hr

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

Procedure: The title compound was prepared according to the procedure of Example 84C substituting ethyl 1-benzyl-6-phenyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate for the product of Example 84B and substituting 2-amino-benzenesulfonamide for the product of Example 84A. 1H NMR (300 MHz, DMSO-d6) δ ppm 5.72 (s, 2 H) 7.28 (m, 6 H) 7.44 (m, 2 H) 7.54 (m, 3 H) 7.67 (m, 1 H) 7.85 (d, J=6.99 Hz, 2 H) 7.92 (dd, J=8.09, 1.47 Hz, 1 H) 7.99 (d, J=8.09 Hz, 1 H) 8.70 (d, J=2.21 Hz, 1 H) 9.17 (d, J=2.21 Hz, 1 H) 12.41 (s, 1 H) 16.80 (s, 1 H).

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

Procedure: The title compound was prepared according to the procedure of Example 84C substituting ethyl 1-benzyl-6-phenyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate for the product of Example 84B and substituting 2-amino-benzenesulfonamide for the product of Example 84A. 1H NMR (300 MHz, DMSO-d6) δ ppm 5.72 (s, 2 H) 7.28 (m, 6 H) 7.44 (m, 2 H) 7.54 (m, 3 H) 7.67 (m, 1 H) 7.85 (d, J=6.99 Hz, 2 H) 7.92 (dd, J=8.09, 1.47 Hz, 1 H) 7.99 (d, J=8.09 Hz, 1 H) 8.70 (d, J=2.21 Hz, 1 H) 9.17 (d, J=2.21 Hz, 1 H) 12.41 (s, 1 H) 16.80 (s, 1 H).

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

Procedure: The title compound was prepared according to the procedure of Example 84C substituting ethyl 1-benzyl-6-chloro-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate for the product of Example 84B and substituting 2-amino-benzenesulfonamide for the product of Example 84A. 1H NMR (300 MHz, DMSO-d6) δ ppm 5.64 (s, 2 H) 7.25 (m, 5 H) 7.44 (t, J=7.72 Hz, 1 H) 7.52 (s, 2 H) 7.67 (m, 1 H) 7.93 (m, 2 H) 8.56 (d, J=2.57 Hz, 1 H) 8.87 (d, J=2.57 Hz, 1 H) 12.34 (s, 1 H) 16.76 (s, 1 H).

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

Procedure: The title compound is prepared according to the procedure of Example 84C substituting the product of Example 174A for the product of Example 84A and substituting the product of Example 99A for the product of example Example 84B.

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

Procedure: The title compound is prepared according to the procedure of Example 84C substituting the product of Example 174A for the product of Example 84A and substituting the product of Example 99A for the product of example Example 84B.

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

Procedure: The title compound is prepared according to the procedure of Example 84C substituting the product of Example 172D for the product of Example 84B and substituting 2-aminosulfonamide for the product of Example 84A.

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

Procedure: The title compound was prepared according to the procedure of Example 84C substituting the product of Example 158C for the product of Example 84B and substituting 2-aminosulfonamide for the product of Example 84A (0.225 g, 86%). MS (DCI) m/z 433 (M+H)+.

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

Procedure: The title compound was prepared according to the procedure of Example 84C substituting the product of Example 158C for the product of Example 84B and substituting 2-aminosulfonamide for the product of Example 84A (0.225 g, 86%). MS (DCI) m/z 433 (M+H)+.