tert-butyl (2R)-2-ethylpiperazine-1-carboxylate

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

Procedure: Following the procedures as described in EXAMPLE 8 and starting with 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and (R)-tert-butyl 2-ethylpiperazine-1-carboxylate, 142 was obtained as an off-white solid (12.7 mg, 10%) over 2 steps. 1H NMR (400 MHz, DMSO) δ 9.18-9.06 (s, 1H), 8.67-8.59 (s, 1H), 8.56-8.49 (s, 1H), 8.31-8.25 (s, 1H), 7.95-7.90 (s, 1H), 7.78-7.70 (t, J=8.1 Hz, 1H), 7.23-7.15 (d, J=7.7 Hz, 1H), 6.84-6.76 (d, J=8.5 Hz, 1H), 4.27-4.15 (m, 4H), 3.10-3.03 (d, J=11.7 Hz, 1H), 3.01-2.93 (td, J=11.8, 3.0 Hz, 1H), 2.86-2.77 (td, J=11.6, 3.0 Hz, 1H), 2.68-2.56 (m, 2H), 1.48-1.38 (m, 5H), 0.94-0.87 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 403.2 [M+H]+

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

Procedure: Following the procedures as described in EXAMPLE 8 and starting with 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and (R)-tert-butyl 2-ethylpiperazine-1-carboxylate, 142 was obtained as an off-white solid (12.7 mg, 10%) over 2 steps. 1H NMR (400 MHz, DMSO) δ 9.18-9.06 (s, 1H), 8.67-8.59 (s, 1H), 8.56-8.49 (s, 1H), 8.31-8.25 (s, 1H), 7.95-7.90 (s, 1H), 7.78-7.70 (t, J=8.1 Hz, 1H), 7.23-7.15 (d, J=7.7 Hz, 1H), 6.84-6.76 (d, J=8.5 Hz, 1H), 4.27-4.15 (m, 4H), 3.10-3.03 (d, J=11.7 Hz, 1H), 3.01-2.93 (td, J=11.8, 3.0 Hz, 1H), 2.86-2.77 (td, J=11.6, 3.0 Hz, 1H), 2.68-2.56 (m, 2H), 1.48-1.38 (m, 5H), 0.94-0.87 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 403.2 [M+H]+

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

Procedure: Following the procedures as described in EXAMPLE 8 and starting with 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and (R)-tert-butyl 2-ethylpiperazine-1-carboxylate, 142 was obtained as an off-white solid (12.7 mg, 10%) over 2 steps. 1H NMR (400 MHz, DMSO) δ 9.18-9.06 (s, 1H), 8.67-8.59 (s, 1H), 8.56-8.49 (s, 1H), 8.31-8.25 (s, 1H), 7.95-7.90 (s, 1H), 7.78-7.70 (t, J=8.1 Hz, 1H), 7.23-7.15 (d, J=7.7 Hz, 1H), 6.84-6.76 (d, J=8.5 Hz, 1H), 4.27-4.15 (m, 4H), 3.10-3.03 (d, J=11.7 Hz, 1H), 3.01-2.93 (td, J=11.8, 3.0 Hz, 1H), 2.86-2.77 (td, J=11.6, 3.0 Hz, 1H), 2.68-2.56 (m, 2H), 1.48-1.38 (m, 5H), 0.94-0.87 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 403.2 [M+H]+