2-(methylamino)-1-phenylethanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A solution of N-(4-chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.06 gm) from Preparation No. 35 in dry NMP (2 mL) containing diisopropylethylarnine (0.04 mL) is treated with α-(methylaminomethyl)-benzyl alcohol (0.04 gm). The reaction mixture is shaken at room temperature for 3 days then concentrated under reduced pressure. The residue is partioned between dichloromethane and water. The separated organic layer is washed with two additional portions of water, brine, dried (Na2SO4) and concentrated under reduced pressure. The residue is adsorbed onto silica and purified by flash column chromatography eluting with 2% to 6% methanol in dichloromethane and then by recrystallization from ethyl acetate-hexanes to afford 0.05 gm of the title compound as a white solid. then concentrated under reduced pressure The separated organic layer is washed with two additional portions of water, brine dried (Na2SO4) concentrated under reduced pressure purified by flash column chromatography eluting with 2% to 6% methanol in dichloromethane by recrystallization from ethyl acetate-hexanes

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

Procedure: A solution of N-(4-chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.06 gm) from Preparation No. 35 in dry NMP (2 mL) containing diisopropylethylarnine (0.04 mL) is treated with α-(methylaminomethyl)-benzyl alcohol (0.04 gm). The reaction mixture is shaken at room temperature for 3 days then concentrated under reduced pressure. The residue is partioned between dichloromethane and water. The separated organic layer is washed with two additional portions of water, brine, dried (Na2SO4) and concentrated under reduced pressure. The residue is adsorbed onto silica and purified by flash column chromatography eluting with 2% to 6% methanol in dichloromethane and then by recrystallization from ethyl acetate-hexanes to afford 0.05 gm of the title compound as a white solid. then concentrated under reduced pressure The separated organic layer is washed with two additional portions of water, brine dried (Na2SO4) concentrated under reduced pressure purified by flash column chromatography eluting with 2% to 6% methanol in dichloromethane by recrystallization from ethyl acetate-hexanes

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

Procedure: Following the general procedure of example 1, 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide (50.0 mg, 0.112 mmol), 2-(methylamino)-1-phenylethanol (129.9 mg, 0.86 mmol) and NaBH(OAc)3 (58.0 mg, 0.303 mmol) were reacted to give the title compound (22.1 mg, 36.6%). were reacted

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To solution of N-(4-chlorobenzyl)-2-(hydroxymethyl)-7-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide (0.300 g) from Example No. 35 in DMF (17 mL) are added DMAP (16 mg), 2,4,6-collidine (0.27 mL), and methanesulfonyl chloride (0.16 mL). The reaction mixture is stirred at room temperature for 1 h and then α-(methylaminomethyl)benzyl alcohol (1.26 g) is added. The mixture is stirred at room temperature for 18 h and is then poured into water (50 mL). The resulting off-white solid is filtered off and purified by column chromatography (CH2Cl2/methanol, 99/1; 97/3) to yield 0.261 g (63%) of the title compound as a pale yellow solid. The mixture is stirred at room temperature for 18 h The resulting off-white solid is filtered off purified by column chromatography (CH2Cl2/methanol, 99/1; 97/3)

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

Procedure: To solution of N-(4-chlorobenzyl)-2-(hydroxymethyl)-7-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide (0.300 g) from Example No. 35 in DMF (17 mL) are added DMAP (16 mg), 2,4,6-collidine (0.27 mL), and methanesulfonyl chloride (0.16 mL). The reaction mixture is stirred at room temperature for 1 h and then α-(methylaminomethyl)benzyl alcohol (1.26 g) is added. The mixture is stirred at room temperature for 18 h and is then poured into water (50 mL). The resulting off-white solid is filtered off and purified by column chromatography (CH2Cl2/methanol, 99/1; 97/3) to yield 0.261 g (63%) of the title compound as a pale yellow solid. The mixture is stirred at room temperature for 18 h The resulting off-white solid is filtered off purified by column chromatography (CH2Cl2/methanol, 99/1; 97/3)