1-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]ethanone

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-[4-([1,3]thiazolo[4,5-b]pyridin-2-yloxy)phenyl]ethyl methanesulfonate (100 mg, 0.29 mmol, 1.0 equiv.) and (1S,4S)-2-acetyl-2,5-diazabicyclo[2.2.1]heptane (48 mg, 0.34 mmol, 1.2 equiv.) in CH3CN (3 mL) was added K2CO3 (39 mg, 0.29 mmol, 1.0 equiv.). The solution was stirred at 80° C. for 16 h and then cooled to rt. Purification by preparative reverse phase HPLC produced a white solid (16%). 1H NMR (500 MHz, CDCl3): 8.57 (dd, J=4.8, 1.7, 1H), 8.03 (dd, J=7.9, 1.7, 1H), 7.36-7.28 (m, 4H), 7.22 (dd, J=7.9, 4.8, 1H), 4.32 (s, 2H), 3.61 (s, 1H), 3.23 (dd, J=8.8, 2.1, 1H), 3.02 (dd, J=9.5, 2.0, 1H), 3.53-3.46 (m, 1H), 2.90-2.77 (m, 4H), 2.73 (d, J=9.4, 1H), 1.92 (d, J=9.6, 1H), 1.77 (d, J=9.3, 1H), 1.62 (s, 1H). MS (ESI): mass calcd. for C20H21N5O2S, 395.14; m/z found, 396.1 [M+H]+. cooled to rt Purification by preparative reverse phase HPLC

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-[4-([1,3]thiazolo[4,5-b]pyridin-2-yloxy)phenyl]ethyl methanesulfonate (100 mg, 0.29 mmol, 1.0 equiv.) and (1S,4S)-2-acetyl-2,5-diazabicyclo[2.2.1]heptane (48 mg, 0.34 mmol, 1.2 equiv.) in CH3CN (3 mL) was added K2CO3 (39 mg, 0.29 mmol, 1.0 equiv.). The solution was stirred at 80° C. for 16 h and then cooled to rt. Purification by preparative reverse phase HPLC produced a white solid (16%). 1H NMR (500 MHz, CDCl3): 8.57 (dd, J=4.8, 1.7, 1H), 8.03 (dd, J=7.9, 1.7, 1H), 7.36-7.28 (m, 4H), 7.22 (dd, J=7.9, 4.8, 1H), 4.32 (s, 2H), 3.61 (s, 1H), 3.23 (dd, J=8.8, 2.1, 1H), 3.02 (dd, J=9.5, 2.0, 1H), 3.53-3.46 (m, 1H), 2.90-2.77 (m, 4H), 2.73 (d, J=9.4, 1H), 1.92 (d, J=9.6, 1H), 1.77 (d, J=9.3, 1H), 1.62 (s, 1H). MS (ESI): mass calcd. for C20H21N5O2S, 395.14; m/z found, 396.1 [M+H]+. cooled to rt Purification by preparative reverse phase HPLC

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-[4-([1,3]thiazolo[4,5-b]pyridin-2-yloxy)phenyl]ethyl methanesulfonate (100 mg, 0.29 mmol, 1.0 equiv.) and (1 S,4S)-2-acetyl-2,5-diazabicyclo[2.2.1]heptane (48 mg, 0.34 mmol, 1.2 equiv.) in CH3CN (3 mL) was added K2CO3 (39 mg, 0.29 mmol, 1.0 equiv.). The solution was stirred at 80° C. for 16 h and then cooled to rt. Purification by preparative reverse phase HPLC produced a white solid (16%). 1H NMR (500 MHz, CDCl3): 8.57 (dd, J=4.8, 1.7, 1H), 8.03 (dd, J=7.9, 1.7, 1H), 7.36-7.28 (m, 4H), 7.22 (dd, J=7.9, 4.8, 1H), 4.32 (s, 2H), 3.61 (s, 1H), 3.23 (dd, J=8.8, 2.1, 1H), 3.02 (dd, J=9.5, 2.0, 1H), 3.53-3.46 (m, 1H), 2.90-2.77 (m, 4H), 2.73 (d, J=9.4, 1H), 1.92 (d, J=9.6, 1H), 1.77 (d, J=9.3, 1H), 1.62 (s, 1H). MS (ESI): mass calcd. for C20H21N6O2S, 395.14; m/z found, 396.1 [M+H]+. cooled to rt Purification by preparative reverse phase HPLC

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-[4-([1,3]thiazolo[4,5-b]pyridin-2-yloxy)phenyl]ethyl methanesulfonate (100 mg, 0.29 mmol, 1.0 equiv.) and (1S,4S)-2-acetyl-2,5-diazabicyclo[2.2.1]heptane (48 mg, 0.34 mmol, 1.2 equiv.) in CH3CN (3 mL) was added K2CO3 (39 mg, 0.29 mmol, 1.0 equiv.). The solution was stirred at 80° C. for 16 h and then cooled to rt. Purification by preparative reverse phase HPLC produced a white solid (16%). 1H NMR (500 MHz, CDCl3): 8.57 (dd, J=4.8, 1.7, 1H), 8.03 (dd, J=7.9, 1.7, 1H), 7.36-7.28 (m, 4H), 7.22 (dd, J=7.9, 4.8, 1H), 4.32 (s, 2H), 3.61 (s, 1H), 3.23 (dd, J=8.8, 2.1, 1H), 3.02 (dd, J=9.5, 2.0, 1H), 3.53-3.46 (m, 1H), 2.90-2.77 (m, 4H), 2.73 (d, J=9.4, 1H), 1.92 (d, J=9.6, 1H), 1.77 (d, J=9.3, 1H), 1.62 (s, 1H). MS (ESI): mass calcd. for C20H21N5O2S, 395.14; m/z found, 396.1 [M+H]+. cooled to rt Purification by preparative reverse phase HPLC