2-[2-(2-methoxyethoxy)ethoxy]ethanamine

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

Procedure: The title compound was prepared from 3-[6′-methyl-4′-(4-trifluoromethyl-phenyl)-[2,2′]bipyridinyl-6-yl]-benzenesulfonyl chloride (example I.2) (0.200 g, 0.409 mmol) by treatment with 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethylamine [CAS-no. 74654-07-2] (0.334 mg, 2.04 mmol) in THF (5 mL) at 23° C. for 16 h. Diluted with EtOAc, washed with 5% citric acid, sat. NaHCO3-sol. and brine, dried organic layer over Na2SO4. Removal of the solvent in vacuum left a crude product, which was purified by silica gel column chromatography with EtOAc followed by trituration with diethyl ether/heptane to give the title compound (0.180 g, 71%) as a light yellow oil. MS (ISP) 616.2 [(M+H)+]. washed with 5% citric acid, sat. NaHCO3-sol Removal of the solvent in vacuum left a crude product, which was purified by silica gel column chromatography with EtOAc

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

Procedure: Prepared from 2-[2-(2-methoxyethoxy)ethoxy]ethanamine and trans-2-methylcyclopropanecarboxylic acid using steps A and B in the procedure described for the synthesis of Intermediate 3.6.1. MS (ES, M+H) 232.

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

Procedure: The title compound was prepared from 3-[6′-methyl-4′-(4-trifluoromethyl-phenyl)-[2,2′]bipyridinyl-6-yl]-benzenesulfonyl chloride (example I.2) (0.200 g, 0.409 mmol) by treatment with 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethylamine [CAS-no. 74654-07-2] (0.334 mg, 2.04 mmol) in THF (5 mL) at 23° C. for 16 h. Diluted with EtOAc, washed with 5% citric acid, sat. NaHCO3-sol. and brine, dried organic layer over Na2SO4. Removal of the solvent in vacuum left a crude product, which was purified by silica gel column chromatography with EtOAc followed by trituration with diethyl ether/heptane to give the title compound (0.180 g, 71%) as a light yellow oil. MS (ISP) 616.2 [(M+H)+]. washed with 5% citric acid, sat. NaHCO3-sol Removal of the solvent in vacuum left a crude product, which was purified by silica gel column chromatography with EtOAc

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

Procedure: T3P, 50 wt % in EtOAc (25 mL, 42.0 mmol) was slowly added to a solution of 3-bromo-5-nitrobenzoic acid (7.05 g, 28.7 mmol), 2-(2-(2-methoxyethoxy)ethoxy)ethanamine (4 g, 24.25 mmol) and Et3N (12 mL, 86 mmol) in EtOAc (50 mL) whilst immersed in an ice-bath. Once the addition was complete, the ice bath was removed and the reaction allowed to stir at rt for 2 h. The mixture was partitioned between sat. aq. NaHCO3 solution (100 mL) and EtOAc (100 mL). The organic layer was washed with aq K2CO3 solution (10 g in 100 mL) and brine (100 mL), before being dried (MgSO4), filtered and concentrated in vacuo to afford the sub-title compound (8.23 g) as a brown oil. immersed in an ice-bath Once the addition the ice bath was removed The mixture was partitioned between sat. aq. NaHCO3 solution (100 mL) and EtOAc (100 mL) The organic layer was washed with aq K2CO3 solution (10 g in 100 mL) and brine (100 mL) before being dried (MgSO4) filtered concentrated in vacuo