2-chloro-N-(3,5-difluorophenyl)acetamide

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

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(6-methoxy-[1,5]naphthyridin-4-yl)-4,5,6,7-tetrahydro-2H-indazol-5-ylamine (30 mg, 0.1 mmol) in DMF (1 mL) were added K2CO3 (40 mg, 0.3 mmol) and 2-chloro-N-(3,5-difluoro-phenyl)-acetamide (20 mg, 0.1 mmol), and the mixture was stirred for 15 h. A catalytic amount of NaI was added and the mixture heated at 50° C. for 15 h. The mixture was diluted with EtOAc (25 mL), washed with brine (4×10 mL), dried (MgSO4) and concentrated. The resulting residue was purified on SiO2 (0-5% CH3OH/CH2Cl2) to provide 30 mg (64%) of the title compound as a pale yellow solid. MS (ESI): exact mass calculated for C24H22F2N6O2, 464.18; m/z found, 465.3 [M+H]+. 1H NMR (500 MHz, CDCl3): 9.30 (br s, 1H), 9.08 (s, 1H), 8.76 (d, J=9.2, 1H), 8.24 (d, J=5.9, 1H), 8.19 (d, J=5.1, 1H), 7.15 (d, J=9.1, 1H), 6.93-6.87 (m, 2H), 6.26 (tt, J=8.9, 2.3, 1H), 3.89 (s, 3H), 3.59 (d, J=17.7, 1H), 3.36 (d, J=17.7, 1H), 3.26-3.23 (m, 1H), 3.08-3.02 (m, 1H), 2.93-2.85 (m, 2H), 2.62 (dd, J=15.7, 5.7, 1H), 2.12-2.08 (m, 1H), 2.00-1.96 (m, 1H). washed with brine (4×10 mL) dried (MgSO4) concentrated The resulting residue was purified on SiO2 (0-5% CH3OH/CH2Cl2)

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

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(6-methoxy-[1,5]naphthyridin-4-yl)-4,5,6,7-tetrahydro-2H-indazol-5-ylamine (30 mg, 0.1 mmol) in DMF (1 mL) were added K2CO3 (40 mg, 0.3 mmol) and 2-chloro-N-(3,5-difluoro-phenyl)-acetamide (20 mg, 0.1 mmol), and the mixture was stirred for 15 h. A catalytic amount of NaI was added and the mixture heated at 50° C. for 15 h. The mixture was diluted with EtOAc (25 mL), washed with brine (4×10 mL), dried (MgSO4) and concentrated. The resulting residue was purified on SiO2 (0-5% CH3OH/CH2Cl2) to provide 30 mg (64%) of the title compound as a pale yellow solid. MS (ESI): exact mass calculated for C24H22F2N6O2, 464.18; m/z found, 465.3 [M+H]+. 1H NMR (500 MHz, CDCl3): 9.30 (br s, 1H), 9.08 (s, 1H), 8.76 (d, J=9.2, 1H), 8.24 (d, J=5.9, 1H), 8.19 (d, J=5.1, 1H), 7.15 (d, J=9.1, 1H), 6.93-6.87 (m, 2H), 6.26 (tt, J=8.9, 2.3, 1H), 3.89 (s, 3H), 3.59 (d, J=17.7, 1H), 3.36 (d, J=17.7, 1H), 3.26-3.23 (m, 1H), 3.08-3.02 (m, 1H), 2.93-2.85 (m, 2H), 2.62 (dd, J=15.7, 5.7, 1H), 2.12-2.08 (m, 1H), 2.00-1.96 (m, 1H). washed with brine (4×10 mL) dried (MgSO4) concentrated The resulting residue was purified on SiO2 (0-5% CH3OH/CH2Cl2)

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(6-methoxy-[1,5]naphthyridin-4-yl)-4,5,6,7-tetrahydro-2H-indazol-5-ylamine (30 mg, 0.1 mmol) in DMF (1 mL) were added K2CO3 (40 mg, 0.3 mmol) and 2-chloro-N-(3,5-difluoro-phenyl)-acetamide (20 mg, 0.1 mmol), and the mixture was stirred for 15 h. A catalytic amount of NaI was added and the mixture heated at 50° C. for 15 h. The mixture was diluted with EtOAc (25 mL), washed with brine (4×10 mL), dried (MgSO4) and concentrated. The resulting residue was purified on SiO2 (0-5% CH3OH/CH2Cl2) to provide 30 mg (64%) of the title compound as a pale yellow solid. MS (ESI): exact mass calculated for C24H22F2N6O2, 464.18; m/z found, 465.3 [M+H]+. 1H NMR (500 MHz, CDCl3): 9.30 (br s, 1H), 9.08 (s, 1H), 8.76 (d, J=9.2, 1H), 8.24 (d, J=5.9, 1H), 8.19 (d, J=5.1, 1H), 7.15 (d, J=9.1, 1H), 6.93-6.87 (m, 2H), 6.26 (tt, J=8.9, 2.3, 1H), 3.89 (s, 3H), 3.59 (d, J=17.7, 1H), 3.36 (d, J=17.7, 1H), 3.26-3.23 (m, 1H), 3.08-3.02 (m, 1H), 2.93-2.85 (m, 2H), 2.62 (dd, J=15.7, 5.7, 1H), 2.12-2.08 (m, 1H), 2.00-1.96 (m, 1H). washed with brine (4×10 mL) dried (MgSO4) concentrated The resulting residue was purified on SiO2 (0-5% CH3OH/CH2Cl2)

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(6-methoxy-[1,5]naphthyridin-4-yl)-4,5,6,7-tetrahydro-2H-indazol-5-ylamine (30 mg, 0.1 mmol) in DMF (1 mL) were added K2CO3 (40 mg, 0.3 mmol) and 2-chloro-N-(3,5-difluoro-phenyl)-acetamide (20 mg, 0.1 mmol), and the mixture was stirred for 15 h. A catalytic amount of NaI was added and the mixture heated at 50° C. for 15 h. The mixture was diluted with EtOAc (25 mL), washed with brine (4×10 mL), dried (MgSO4) and concentrated. The resulting residue was purified on SiO2 (0-5% CH3OH/CH2Cl2) to provide 30 mg (64%) of the title compound as a pale yellow solid. MS (ESI): exact mass calculated for C24H22F2N6O2, 464.18; m/z found, 465.3 [M+H]+. 1H NMR (500 MHz, CDCl3): 9.30 (br s, 1H), 9.08 (s, 1H), 8.76 (d, J=9.2, 1H), 8.24 (d, J=5.9, 1H), 8.19 (d, J=5.1, 1H), 7.15 (d, J=9.1, 1H), 6.93-6.87 (m, 2H), 6.26 (tt, J=8.9, 2.3, 1H), 3.89 (s, 3H), 3.59 (d, J=17.7, 1H), 3.36 (d, J=17.7, 1H), 3.26-3.23 (m, 1H), 3.08-3.02 (m, 1H), 2.93-2.85 (m, 2H), 2.62 (dd, J=15.7, 5.7, 1H), 2.12-2.08 (m, 1H), 2.00-1.96 (m, 1H). washed with brine (4×10 mL) dried (MgSO4) concentrated The resulting residue was purified on SiO2 (0-5% CH3OH/CH2Cl2)