1-(cyclohexylamino)propan-2-yl benzoate

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

Procedure: To a stirred solution of benzoic acid 2-cyclohexylamino-1-methyl-ethyl ester (1.0 g, 3.8 mmol) in DCE (20 mL) were added successively K2CO3 (2.11 g, 15.2 mmol) and ethyl iodide (1.8 mL, 22 mmol). The resulting mixture was heated at 50° C. for 16 hours in a sealed tube. Ethyl iodide (1.8 mL) was again added and the reaction mixture heated at 60° C. for another 24 hours. The reaction mixture was filtered and washed 5% methanol-DCM. The filtrate was concentrated and the crude material was purified by Combiflash® chromatography eluting with 6-7% methanol/DCM to provide 1-(cyclohexyl(ethyl)amino)propan-2-yl benzoate. Yield: 1.04 g (94.70%). 1H NMR (DMSO-d5) δ 7.95 (d, J=7 Hz, 2H), 7.64 (t, J=7 Hz, 1H), 7.52 (t, J=8 Hz, 2H), 5.08-5.04 (m, 1H), 2.68-2.62 (m, 1H), 2.55-2.40 (m, 4H), 1.70-1.53 (m, 5H), 1.26 (d, J=6 Hz, 3H), 1.19-1.07 (m, 5H), 0.93 (t, J=7 Hz, 3H). LCMS: m/z=290.4 [M+H], RT=3.93 min, (Column: Y, Program: P1) the reaction mixture heated at 60° C. for another 24 hours The reaction mixture was filtered washed 5% methanol-DCM The filtrate was concentrated the crude material was purified by Combiflash® chromatography eluting with 6-7% methanol/DCM

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

Procedure: To a stirred solution of benzoic acid 2-cyclohexylamino-1-methyl-ethyl ester (1.0 g, 3.8 mmol) in DCE (20 mL) were added successively K2CO3 (2.11 g, 15.2 mmol) and ethyl iodide (1.8 mL, 22 mmol). The resulting mixture was heated at 50° C. for 16 hours in a sealed tube. Ethyl iodide (1.8 mL) was again added and the reaction mixture heated at 60° C. for another 24 hours. The reaction mixture was filtered and washed 5% methanol-DCM. The filtrate was concentrated and the crude material was purified by Combiflash® chromatography eluting with 6-7% methanol/DCM to provide 1-(cyclohexyl(ethyl)amino)propan-2-yl benzoate. Yield: 1.04 g (94.70%). 1H NMR (DMSO-d5) δ 7.95 (d, J=7 Hz, 2H), 7.64 (t, J=7 Hz, 1H), 7.52 (t, J=8 Hz, 2H), 5.08-5.04 (m, 1H), 2.68-2.62 (m, 1H), 2.55-2.40 (m, 4H), 1.70-1.53 (m, 5H), 1.26 (d, J=6 Hz, 3H), 1.19-1.07 (m, 5H), 0.93 (t, J=7 Hz, 3H). LCMS: m/z=290.4 [M+H], RT=3.93 min, (Column: Y, Program: P1) the reaction mixture heated at 60° C. for another 24 hours The reaction mixture was filtered washed 5% methanol-DCM The filtrate was concentrated the crude material was purified by Combiflash® chromatography eluting with 6-7% methanol/DCM

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

Procedure: To a stirred solution of benzoic acid 2-cyclohexylamino-1-methyl-ethyl ester (1.0 g, 3.8 mmol) in DCE (20 mL) were added successively K2CO3 (2.11 g, 15.2 mmol) and ethyl iodide (1.8 mL, 22 mmol). The resulting mixture was heated at 50° C. for 16 hours in a sealed tube. Ethyl iodide (1.8 mL) was again added and the reaction mixture heated at 60° C. for another 24 hours. The reaction mixture was filtered and washed 5% methanol-DCM. The filtrate was concentrated and the crude material was purified by Combiflash® chromatography eluting with 6-7% methanol/DCM to provide 1-(cyclohexyl(ethyl)amino)propan-2-yl benzoate. Yield: 1.04 g (94.70%). 1H NMR (DMSO-d6) δ 7.95 (d, J=7 Hz, 2 H), 7.64 (t, J=7 Hz, 1 H), 7.52 (t, J=8 Hz, 2 H), 5.08-5.04 (m, 1 H), 2.68-2.62 (m, 1 H), 2.55-2.40 (m, 4 H), 1.70-1.53 (m, 5 H), 1.26 (d, J=6 Hz, 3 H), 1.19-1.07 (m, 5 H), 0.93 (t, J=7 Hz, 3 H). LCMS: m/z=290.4 [M+H], RT=3.93 min, (Column: Y, Program: P1) the reaction mixture heated at 60° C. for another 24 hours The reaction mixture was filtered washed 5% methanol-DCM The filtrate was concentrated the crude material was purified by Combiflash® chromatography eluting with 6-7% methanol/DCM

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

Procedure: To a stirred solution of benzoic acid 2-cyclohexylamino-1-methyl-ethyl ester (1.0 g, 3.8 mmol) in DCE (20 mL) were added successively K2CO3 (2.11 g, 15.2 mmol) and ethyl iodide (1.8 mL, 22 mmol). The resulting mixture was heated at 50° C. for 16 hours in a sealed tube. Ethyl iodide (1.8 mL) was again added and the reaction mixture heated at 60° C. for another 24 hours. The reaction mixture was filtered and washed 5% methanol-DCM. The filtrate was concentrated and the crude material was purified by Combiflash® chromatography eluting with 6-7% methanol/DCM to provide 1-(cyclohexyl(ethyl)amino)propan-2-yl benzoate. Yield: 1.04 g (94.70%). 1H NMR (DMSO-d5) δ 7.95 (d, J=7 Hz, 2H), 7.64 (t, J=7 Hz, 1H), 7.52 (t, J=8 Hz, 2H), 5.08-5.04 (m, 1H), 2.68-2.62 (m, 1H), 2.55-2.40 (m, 4H), 1.70-1.53 (m, 5H), 1.26 (d, J=6 Hz, 3H), 1.19-1.07 (m, 5H), 0.93 (t, J=7 Hz, 3H). LCMS: m/z=290.4 [M+H], RT=3.93 min, (Column: Y, Program: P1) the reaction mixture heated at 60° C. for another 24 hours The reaction mixture was filtered washed 5% methanol-DCM The filtrate was concentrated the crude material was purified by Combiflash® chromatography eluting with 6-7% methanol/DCM