1-(1-ethylpyrrolidin-2-yl)-N-methylmethanamine

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

Procedure: The title compound was prepared in a manner similar to Example 112 using 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid and 1-(1-ethylpyrrolidin-2-yl)-N-methylmethanamine 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92-1.36 (m, 3 H) 1.60-1.96 (m, 2 H) 2.11 (br. s., 1 H) 2.43 (s, 3 H) 2.60-2.95 (m, 2 H) 3.06 (br. s., 3 H) 3.12-3.58 (m, 5 H) 3.58-3.84 (m, 1 H) 7.54 (d, J=8.08 Hz, 1 H) 7.59 (s, 1 H) 7.93 (s, 1 H) 7.98 (dd, J=8.72, 2.15 Hz, 1 H) 8.07 (br. s., 1 H) 8.48 (d, J=8.08 Hz, 1 H) 8.50-8.54 (m, 1 H); ESI-MS m/z [M+H]+ 445.2.

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

Procedure: The title compound was prepared in a manner similar to Example 112 using 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid and 1-(1-ethylpyrrolidin-2-yl)-N-methylmethanamine. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92-1.36 (m, 3H) 1.60-1.96 (m, 2H) 2.11 (br. s., 1H) 2.43 (s, 3H) 2.60-2.95 (m, 2H) 3.06 (br. s., 3H) 3.12-3.58 (m, 5H) 3.58-3.84 (m, 1H) 7.54 (d, J=8.08 Hz, 1H) 7.59 (s, 1H) 7.93 (s, 1H) 7.98 (dd, J=8.72, 2.15 Hz, 1H) 8.07 (br. s., 1H) 8.48 (d, J=8.08 Hz, 1H) 8.50-8.54 (m, 1H); ESI-MS m/z [M+H]+ 445.2.

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

Procedure: The title compound was prepared in a manner similar to Example 112 using 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid and 1-(1-ethylpyrrolidin-2-yl)-N-methylmethanamine 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92-1.36 (m, 3 H) 1.60-1.96 (m, 2 H) 2.11 (br. s., 1 H) 2.43 (s, 3 H) 2.60-2.95 (m, 2 H) 3.06 (br. s., 3 H) 3.12-3.58 (m, 5 H) 3.58-3.84 (m, 1 H) 7.54 (d, J=8.08 Hz, 1 H) 7.59 (s, 1 H) 7.93 (s, 1 H) 7.98 (dd, J=8.72, 2.15 Hz, 1 H) 8.07 (br. s., 1 H) 8.48 (d, J=8.08 Hz, 1 H) 8.50-8.54 (m, 1 H); ESI-MS m/z [M+H]+ 445.2.

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

Procedure: The title compound was prepared in a manner similar to Example 112 using 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid and 1-(1-ethylpyrrolidin-2-yl)-N-methylmethanamine. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92-1.36 (m, 3H) 1.60-1.96 (m, 2H) 2.11 (br. s., 1H) 2.43 (s, 3H) 2.60-2.95 (m, 2H) 3.06 (br. s., 3H) 3.12-3.58 (m, 5H) 3.58-3.84 (m, 1H) 7.54 (d, J=8.08 Hz, 1H) 7.59 (s, 1H) 7.93 (s, 1H) 7.98 (dd, J=8.72, 2.15 Hz, 1H) 8.07 (br. s., 1H) 8.48 (d, J=8.08 Hz, 1H) 8.50-8.54 (m, 1H); ESI-MS m/z [M+H]+ 445.2.