4-(methylsulfonylmethyl)cyclohexan-1-amine

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-[3-(2-methylsulfinyl-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-8-yl]-propan-2-ol (75 mg), 4-methanesulfonylmethyl-cyclohexylamine (162 mg), and TEA (0.165 mL) in NMP (2 mL) was stirred at 100° C. overnight. The reaction mixture was then cooled to RT, and diluted with water. The resulting precipitate was filtered and dried, then purified by ISCO using 100% DCM to 10% MeOH/DCM. The fractions were collected, concentrated, and titurated with EtOAc. The resulting solid was filtered and dried at 50° C. under vacuum overnight to provide 2-{3-[2-(4-methanesulfonylmethyl-cyclohexylamino)-pyrimidin-4-yl]-imidazo[1,2-a]pyridin-8-yl}-propan-2-ol (Compound 1, 55.5 mg). Mp=223-224° C. The reaction mixture was then cooled to RT The resulting precipitate was filtered dried purified by ISCO The fractions were collected concentrated The resulting solid was filtered dried at 50° C. under vacuum overnight

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-[3-(2-methylsulfinyl-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-8-yl]-propan-2-ol (75 mg), 4-methanesulfonylmethyl-cyclohexylamine (162 mg), and TEA (0.165 mL) in NMP (2 mL) was stirred at 100° C. overnight. The reaction mixture was then cooled to RT, and diluted with water. The resulting precipitate was filtered and dried, then purified by ISCO using 100% DCM to 10% MeOH/DCM. The fractions were collected, concentrated, and titurated with EtOAc. The resulting solid was filtered and dried at 50° C. under vacuum overnight to provide 2-{3-[2-(4-methanesulfonylmethyl-cyclohexylamino)-pyrimidin-4-yl]-imidazo[1,2-a]pyridin-8-yl}-propan-2-ol (Compound 1, 55.5 mg). Mp=223-224° C. The reaction mixture was then cooled to RT The resulting precipitate was filtered dried purified by ISCO The fractions were collected concentrated The resulting solid was filtered dried at 50° C. under vacuum overnight

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

Procedure: (4-Methanesulfonylmethyl-cyclohexyl)-carbamic acid benzyl ester (0.54 g, 1.66 mmol) in ethanol (15 mL, IMS grade) under nitrogen was treated with 10% palladium/carbon (0.18 g, 0.17 mmol). The mixture was purged with hydrogen gas and was stirred under an atmosphere of hydrogen (balloon) for 16 hours. The catalyst was filtered off through Celite® and the filter cake rinsed several times with ethanol. The filtrate was concentrated and then purified by column chromatography on Isolute® SCX-2 cartridge (eluting with MeOH then 2M NH3 in MeOH). The relevant fractions were combined concentrated under vacuum to afford 0.32 g (95%) 4-methanesulfonylmethyl-cyclohexylamine as clear oil that was used without further purification. LCMS (Method I, ESI): RT=0.35 min, m+H=191.9. The mixture was purged with hydrogen gas The catalyst was filtered off through Celite® the filter cake rinsed several times with ethanol The filtrate was concentrated purified by column chromatography on Isolute® SCX-2 cartridge ( eluting with MeOH The relevant fractions were combined concentrated under vacuum

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-[3-(2-methylsulfinyl-pyrimidin-4-yl)-imidazo[1,2-a]pyridin-8-yl]-propan-2-ol (75 mg), 4-methanesulfonylmethyl-cyclohexylamine (162 mg), and TEA (0.165 mL) in NMP (2 mL) was stirred at 100° C. overnight. The reaction mixture was then cooled to RT, and diluted with water. The resulting precipitate was filtered and dried, then purified by ISCO using 100% DCM to 10% MeOH/DCM. The fractions were collected, concentrated, and titurated with EtOAc. The resulting solid was filtered and dried at 50° C. under vacuum overnight to provide 2-{3-[2-(4-methanesulfonylmethyl-cyclohexylamino)-pyrimidin-4-yl]-imidazo[1,2-a]pyridin-8-yl}-propan-2-ol (Compound 1, 55.5 mg). Mp=223-224° C. The reaction mixture was then cooled to RT The resulting precipitate was filtered dried purified by ISCO The fractions were collected concentrated The resulting solid was filtered dried at 50° C. under vacuum overnight