2-amino-6-[(4-methoxyphenyl)methoxy]benzonitrile

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

Procedure: To a solution of chlorosulfonyl isocyanate (212 mg, 1.50 mmol) in CH2Cl2 (0.55 mL) at 0° C., was added formic acid (0.575 mL) under N2. The reaction was stirred for 30 min, and a solution of 2-amino-6-(4-methoxybenzyloxy)benzonitrile (Example 114b) (191 mg, 0.75 mmol) in CH2Cl2 (4 mL) was added at 0° C., followed by Et3N (0.627 mL, 4.50 mmol). After 30 min, the reaction was concentrated in vacuo and diluted with water. The pH was adjusted to 7 with concentrated HCl, and purified by reverse phase HPLC (10-90% acetonitrile in water) to provide 2-sulfamoylamino-6-(4-methoxybenzyloxy)benzonitrile (130 mg, 52%). 1H NMR (400 MHz, MeOD) δ 3.80 (s, 3H), 5.15 (s, 2H), 6.88 (d, J=8.1 Hz 1H), 6.94 (m, 2H), 7.40 (m, 2H), 7.48 (t, J=8.7 Hz, 1H), 7.75 (dd, J=8.6, 0.8 Hz, 1H). After 30 min the reaction was concentrated in vacuo diluted with water purified by reverse phase HPLC (10-90% acetonitrile in water)

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

Procedure: To a solution of chlorosulfonyl isocyanate (212 mg, 1.50 mmol) in CH2Cl2 (0.55 mL) at 0° C., was added formic acid (0.575 mL) under N2. The reaction was stirred for 30 min, and a solution of 2-amino-6-(4-methoxybenzyloxy)benzonitrile (Example 114b) (191 mg, 0.75 mmol) in CH2Cl2 (4 mL) was added at 0° C., followed by Et3N (0.627 mL, 4.50 mmol). After 30 min, the reaction was concentrated in vacuo and diluted with water. The pH was adjusted to 7 with concentrated HCl, and purified by reverse phase HPLC (10-90% acetonitrile in water) to provide 2-sulfamoylamino-6-(4-methoxybenzyloxy)benzonitrile (130 mg, 52%). 1H NMR (400 MHz, MeOD) δ 3.80 (s, 3H), 5.15 (s, 2H), 6.88 (d, J=8.1 Hz 1H), 6.94 (m, 2H), 7.40 (m, 2H), 7.48 (t, J=8.7 Hz, 1H), 7.75 (dd, J=8.6, 0.8 Hz, 1H). After 30 min the reaction was concentrated in vacuo diluted with water purified by reverse phase HPLC (10-90% acetonitrile in water)

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

Procedure: To a solution of chlorosulfonyl isocyanate (212 mg, 1.50 mmol) in CH2Cl2 (0.55 mL) at 0° C., was added formic acid (0.575 mL) under N2. The reaction was stirred for 30 min, and a solution of 2-amino-6-(4-methoxybenzyloxy)benzonitrile (Example 114b) (191 mg, 0.75 mmol) in CH2Cl2 (4 mL) was added at 0° C., followed by Et3N (0.627 mL, 4.50 mmol). After 30 min, the reaction was concentrated in vacuo and diluted with water. The pH was adjusted to 7 with concentrated HCl, and purified by reverse phase HPLC (10-90% acetonitrile in water) to provide 2-sulfamoylamino-6-(4-methoxybenzyloxy)benzonitrile (130 mg, 52%). 1H NMR (400 MHz, MeOD) δ 3.80 (s, 3H), 5.15 (s, 2H), 6.88 (d, J=8.1 Hz 1H), 6.94 (m, 2H), 7.40 (m, 2H), 7.48 (t, J=8.7 Hz, 1H), 7.75 (dd, J=8.6, 0.8 Hz, 1H). After 30 min the reaction was concentrated in vacuo diluted with water purified by reverse phase HPLC (10-90% acetonitrile in water)

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

Procedure: To a solution of chlorosulfonyl isocyanate (212 mg, 1.50 mmol) in CH2Cl2 (0.55 mL) at 0° C., was added formic acid (0.575 mL) under N2. The reaction was stirred for 30 min, and a solution of 2-amino-6-(4-methoxybenzyloxy)benzonitrile (Example 114b) (191 mg, 0.75 mmol) in CH2Cl2 (4 mL) was added at 0° C., followed by Et3N (0.627 mL, 4.50 mmol). After 30 min, the reaction was concentrated in vacuo and diluted with water. The pH was adjusted to 7 with concentrated HCl, and purified by reverse phase HPLC (10-90% acetonitrile in water) to provide 2-sulfamoylamino-6-(4-methoxybenzyloxy)benzonitrile (130 mg, 52%). 1H NMR (400 MHz, MeOD) δ 3.80 (s, 3H), 5.15 (s, 2H), 6.88 (d, J=8.1 Hz 1H), 6.94 (m, 2H), 7.40 (m, 2H), 7.48 (t, J=8.7 Hz, 1H), 7.75 (dd, J=8.6, 0.8 Hz, 1H). After 30 min the reaction was concentrated in vacuo diluted with water purified by reverse phase HPLC (10-90% acetonitrile in water)

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

Procedure: To a solution of chlorosulfonyl isocyanate (212 mg, 1.50 mmol) in CH2Cl2 (0.55 mL) at 0° C., was added formic acid (0.575 mL) under N2. The reaction was stirred for 30 min, and a solution of 2-amino-6-(4-methoxybenzyloxy)benzonitrile (Example 114b) (191 mg, 0.75 mmol) in CH2Cl2 (4 mL) was added at 0° C., followed by Et3N (0.627 mL, 4.50 mmol). After 30 min, the reaction was concentrated in vacuo and diluted with water. The pH was adjusted to 7 with concentrated HCl, and purified by reverse phase HPLC (10-90% acetonitrile in water) to provide 2-sulfamoylamino-6-(4-methoxybenzyloxy)benzonitrile (130 mg, 52%). 1H NMR (400 MHz, MeOD) δ 3.80 (s, 3H), 5.15 (s, 2H), 6.88 (d, J=8.1 Hz 1H), 6.94 (m, 2H), 7.40 (m, 2H), 7.48 (t, J=8.7 Hz, 1H), 7.75 (dd, J=8.6, 0.8 Hz, 1H). After 30 min the reaction was concentrated in vacuo diluted with water purified by reverse phase HPLC (10-90% acetonitrile in water)

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

Procedure: To a solution of chlorosulfonyl isocyanate (212 mg, 1.50 mmol) in CH2Cl2 (0.55 mL) at 0° C., was added formic acid (0.575 mL) under N2. The reaction was stirred for 30 min, and a solution of 2-amino-6-(4-methoxybenzyloxy)benzonitrile (Example 114b) (191 mg, 0.75 mmol) in CH2Cl2 (4 mL) was added at 0° C., followed by Et3N (0.627 mL, 4.50 mmol). After 30 min, the reaction was concentrated in vacuo and diluted with water. The pH was adjusted to 7 with concentrated HCl, and purified by reverse phase HPLC (10-90% acetonitrile in water) to provide 2-sulfamoylamino-6-(4-methoxybenzyloxy)benzonitrile (130 mg, 52%). 1H NMR (400 MHz, MeOD) δ 3.80 (s, 3H), 5.15 (s, 2H), 6.88 (d, J=8.1 Hz 1H), 6.94 (m, 2H), 7.40 (m, 2H), 7.48 (t, J=8.7 Hz, 1H), 7.75 (dd, J=8.6, 0.8 Hz, 1H). After 30 min the reaction was concentrated in vacuo diluted with water purified by reverse phase HPLC (10-90% acetonitrile in water)