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

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

Procedure: A suspension of 362 (0.90 g, 2.3 mmol), amine 363 (0.93 g, 5.7 mmol) [amine 363 has been synthesized according to the procedures used for the synthesis of amines 322 (scheme 18) and 326 (scheme 20)] and acetic acid (0.26 ml, 4.6 mmol) in dichloromethane (50 ml) was stirred for 1 h at room temperature. Then sodium triacetoxyborohydride (1.45 g, 6.85 mmol) was added and the mixture was stirred at r.t. for 16 h. A further amount of sodium triacetoxyborohydride (1.5 g) was then added, and stirring continued for 2 h. The reaction mixture was partitioned between dichloromethane and 1N HCl. The organic phase was discarded. The aqueous phase was basified (pH=13) with 3M NaOH, and extracted with dichloromethane. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated to yield 364 (0.72 g, 58%) as a yellow solid. LRMS (M+H): 542.4 has been synthesized the mixture was stirred at r.t. for 16 h stirring continued for 2 h The reaction mixture was partitioned between dichloromethane and 1N HCl extracted with dichloromethane The organic extract was dried over anhydrous sodium sulfate filtered concentrated

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

Procedure: A suspension of 362 (0.90 g, 2.3 mmol), amine 363 (0.93 g, 5.7 mmol) [amine 363 has been synthesized according to the procedures used for the synthesis of amines 322 (scheme 18) and 326 (scheme 20)] and acetic acid (0.26 ml, 4.6 mmol) in dichloromethane (50 ml) was stirred for 1 h at room temperature. Then sodium triacetoxyborohydride (1.45 g, 6.85 mmol) was added and the mixture was stirred at r.t. for 16 h. A further amount of sodium triacetoxyborohydride (1.5 g) was then added, and stirring continued for 2 h. The reaction mixture was partitioned between dichloromethane and 1N HCl. The organic phase was discarded. The aqueous phase was basified (pH=13) with 3M NaOH, and extracted with dichloromethane. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated to yield 364 (0.72 g, 58%) as a yellow solid. LRMS (M+H): 542.4 has been synthesized the mixture was stirred at r.t. for 16 h stirring continued for 2 h The reaction mixture was partitioned between dichloromethane and 1N HCl extracted with dichloromethane The organic extract was dried over anhydrous sodium sulfate filtered concentrated

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

Procedure: A suspension of 362 (0.90 g, 2.3 mmol), amine 363 (0.93 g, 5.7 mmol) [amine 363 has been synthesized according to the procedures used for the synthesis of amines 322 (scheme 18) and 326 (scheme 20)] and acetic acid (0.26 ml, 4.6 mmol) in dichloromethane (50 ml) was stirred for 1 h at room temperature. Then sodium triacetoxyborohydride (1.45 g, 6.85 mmol) was added and the mixture was stirred at r.t. for 16 h. A further amount of sodium triacetoxyborohydride (1.5 g) was then added, and stirring continued for 2 h. The reaction mixture was partitioned between dichloromethane and 1N HCl. The organic phase was discarded. The aqueous phase was basified (pH=13) with 3M NaOH, and extracted with dichloromethane. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated to yield 364 (0.72 g, 58%) as a yellow solid. LRMS (M+H): 542.4 has been synthesized the mixture was stirred at r.t. for 16 h stirring continued for 2 h The reaction mixture was partitioned between dichloromethane and 1N HCl extracted with dichloromethane The organic extract was dried over anhydrous sodium sulfate filtered concentrated

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) (0.210 g, 0.429 mmol) by treatment with 2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethylamine [CAS-no. 85030-56-4] (0.089 g, 0.429 mmol) and Et3N (0.180 mL, 1.287 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 gave the title compound (0.080 g, 28%) as an orange oil. MS (ISP) 659.7 [(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: The title compound was prepared from 3-[6′-methyl-4′-(4-trifluoromethyl-phenyl)-[2,2′]bipyridinyl-6-yl]-benzenesulfonyl chloride (example I.2) (0.210 g, 0.429 mmol) by treatment with 2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethylamine [CAS-no. 85030-56-4] (0.089 g, 0.429 mmol) and Et3N (0.180 mL, 1.287 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 gave the title compound (0.080 g, 28%) as an orange oil. MS (ISP) 659.7 [(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: A suspension of 362 (0.90 g, 2.3 mmol), amine 363 (0.93 g, 5.7 mmol) [amine 363 has been synthesized according to the procedures used for the synthesis of amines 322 (scheme 18) and 326 (scheme 20)] and acetic acid (0.26 ml, 4.6 mmol) in dichloromethane (50 ml) was stirred for 1 h at room temperature. Then sodium triacetoxyborohydride (1.45 g, 6.85 mmol) was added and the mixture was stirred at r.t. for 16 h. A further amount of sodium triacetoxyborohydride (1.5 g) was then added, and stirring continued for 2 h. The reaction mixture was partitioned between dichloromethane and 1N HCl. The organic phase was discarded. The aqueous phase was basified (pH=13) with 3M NaOH, and extracted with dichloromethane. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated to yield 364 (0.72 g, 58%) as a yellow solid. LRMS (M+H): 542.4 has been synthesized the mixture was stirred at r.t. for 16 h stirring continued for 2 h The reaction mixture was partitioned between dichloromethane and 1N HCl extracted with dichloromethane The organic extract was dried over anhydrous sodium sulfate filtered concentrated