2-(2-aminoethyl)phenol

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

Procedure: 10% Palladium-carbon catalyst (water content 50%, 42 mg) was added to a solution of 2-(2-benzyloxyphenyl)ethylamine (415 mg, 1.826 mmol, 1.0 eq) in THF (10 ml), and the mixture was stirred for 2 hours at room temperature in a stream of hydrogen. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to give 2-(2-hydroxyphenyl)ethylamine (230 mg, 91.8%). The reaction mixture was filtered through Celite the filtrate was concentrated under reduced pressure

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

Procedure: 10% Palladium-carbon catalyst (water content 50%, 42 mg) was added to a solution of 2-(2-benzyloxyphenyl)ethylamine (415 mg, 1.826 mmol, 1.0 eq) in THF (10 ml), and the mixture was stirred for 2 hours at room temperature in a stream of hydrogen. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to give 2-(2-hydroxyphenyl)ethylamine (230 mg, 91.8%). The reaction mixture was filtered through Celite the filtrate was concentrated under reduced pressure

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

Procedure: Intermediate 4 was coupled with 2-(2-amino-ethyl)-phenol following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 456. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.30 ppm) δ 8.3 (m, 3H) 7.8 (d, 1H) 7.6 (m, 1H) 7.5 (d, 1H) 7.1 (d, 1H) 7.0 (m, 1H) 6.7 (d, 2H) 4.5 (s, 2H) 3.9 (m, 2H) 3.4 (m, 2H) 3.0 (m, 5H) 2.8 (m, 2H) 1.8 (m, 2H).

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

Procedure: Intermediate 4 was coupled with 2-(2-amino-ethyl)-phenol following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 456. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.30 ppm) δ 8.3 (m, 3H) 7.8 (d, 1H) 7.6 (m, 1H) 7.5 (d, 1H) 7.1 (d, 1H) 7.0 (m, 1H) 6.7 (d, 2H) 4.5 (s, 2H) 3.9 (m, 2H) 3.4 (m, 2H) 3.0 (m, 5H) 2.8 (m, 2H) 1.8 (m, 2H).

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

Procedure: Intermediate 4 was coupled with 2-(2-amino-ethyl)-phenol following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 456. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.30 ppm) δ 8.3 (m, 3H) 7.8 (d, 1H) 7.6 (m, 1H) 7.5 (d, 1H) 7.1 (d, 1H) 7.0 (m, 1H) 6.7 (d, 2H) 4.5 (s, 2H) 3.9 (m, 2H) 3.4 (m, 2H) 3.0 (m, 5H) 2.8 (m, 2H) 1.8 (m, 2H).

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

Procedure: Method 1, Example 205 is substantially repeated except for utilizing 5′-ethyl-2′-methyl-6′-oxo-1′,6′-dihydro-[3,3′]bipyridinyl-5-carboxylic acid and 2-(2-hydroxy-phenyl)-ethyl-amine to afford the title compound. MS: m/e=378 (M+H).

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

Procedure: 10% Palladium-carbon catalyst (water content 50%, 42 mg) was added to a solution of 2-(2-benzyloxyphenyl)ethylamine (415 mg, 1.826 mmol, 1.0 eq) in THF (10 ml), and the mixture was stirred for 2 hours at room temperature in a stream of hydrogen. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to give 2-(2-hydroxyphenyl)ethylamine (230 mg, 91.8%). The reaction mixture was filtered through Celite the filtrate was concentrated under reduced pressure

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

Procedure: Intermediate 4 was coupled with 2-(2-amino-ethyl)-phenol following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 456. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.30 ppm) δ 8.3 (m, 3H) 7.8 (d, 1H) 7.6 (m, 1H) 7.5 (d, 1H) 7.1 (d, 1H) 7.0 (m, 1H) 6.7 (d, 2H) 4.5 (s, 2H) 3.9 (m, 2H) 3.4 (m, 2H) 3.0 (m, 5H) 2.8 (m, 2H) 1.8 (m, 2H).