2-ethoxy-N-(2-ethoxyethyl)ethanamine

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: Bis-(2-ethoxyethyl)amine (560 μL, 3.13 mmol) was added to a solution of trimethylaluminum in toluene (1.56 mL, 3.13 mmol) and the solution was stirred for 20 minutes. A portion (424 μL) of the resulting solution was added to a solution of 7-chloro-3-(ethoxycarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione (100 mg, 0.313 mmol) in toluene (780 μL). The resulting solution was stirred for 4.5 hours at room temperature and then quenched with aqueous hydrochloric acid (1.5 mL, 1N) and water (20 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL) and the organic layers were concentrated on a rotary evaporator. The crude product was purified by flash chromatography eluting with chloroform:2-propanol (99:1-80:20) to give the title compound (60.8 mg, 45% yield, m.p. 202° C.). The resulting solution was stirred for 4.5 hours at room temperature quenched with aqueous hydrochloric acid (1.5 mL, 1N) and water (20 mL) The aqueous layer was extracted with ethyl acetate (3×50 mL) the organic layers were concentrated on a rotary evaporator The crude product was purified by flash chromatography eluting with chloroform:2-propanol (99:1-80:20)

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

Procedure: Bis-(2-ethoxyethyl)amine (560 μL, 3.13 mmol) was added to a solution of trimethylaluminum in toluene (1.56 mL, 3.13 mmol) and the solution was stirred for 20 minutes. A portion (424 μL) of the resulting solution was added to a solution of 7-chloro-3-(ethoxycarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione (100 mg, 0.313 mmol) in toluene (780 μL). The resulting solution was stirred for 4.5 hours at room temperature and then quenched with aqueous hydrochloric acid (1.5 mL, 1N) and water (20 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL) and the organic layers were concentrated on a rotary evaporator. The crude product was purified by flash chromatography eluting with chloroform:2-propanol (99:1-80:20) to give the title compound (60.8 mg, 45% yield, m.p. 202° C.). The resulting solution was stirred for 4.5 hours at room temperature quenched with aqueous hydrochloric acid (1.5 mL, 1N) and water (20 mL) The aqueous layer was extracted with ethyl acetate (3×50 mL) the organic layers were concentrated on a rotary evaporator The crude product was purified by flash chromatography eluting with chloroform:2-propanol (99:1-80:20)

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

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

Procedure: Bis-(2-ethoxyethyl)amine (560 μL, 3.13 mmol) was added to a solution of trimethylaluminum in toluene (1.56 mL, 3.13 mmol) and the solution was stirred for 20 minutes. A portion (424 μL) of the resulting solution was added to a solution of 7-chloro-3-(ethoxycarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione (100 mg, 0.313 mmol) in toluene (780 μL). The resulting solution was stirred for 4.5 hours at room temperature and then quenched with aqueous hydrochloric acid (1.5 mL, 1N) and water (20 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL) and the organic layers were concentrated on a rotary evaporator. The crude product was purified by flash chromatography eluting with chloroform:2-propanol (99:1-80:20) to give the title compound (60.8 mg, 45% yield, m.p. 202° C.). The resulting solution was stirred for 4.5 hours at room temperature quenched with aqueous hydrochloric acid (1.5 mL, 1N) and water (20 mL) The aqueous layer was extracted with ethyl acetate (3×50 mL) the organic layers were concentrated on a rotary evaporator The crude product was purified by flash chromatography eluting with chloroform:2-propanol (99:1-80:20)

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

Procedure: In a manner analogous to the method described in example 99, {4-[(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-piperazin-1-yl}-acetic acid was coupled with bis-(2-ethoxy-ethyl)-amine (TCI-US) to give the title compound. HR-MS (ES, m/z) calculated for C43H59Cl2N6O5 [(M+H)+] 809.3919, observed 809.3118.

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

Procedure: In a manner analogous to the method described in example 163, {1-[(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-piperidin-4-yl}-acetic acid was coupled with bis-(2-ethoxy-ethyl)-amine (TCI-US) to give the title compound. HR-MS (ES, m/z) calculated for C44H60Cl2N5O5 [(M+H)+] 808.3966, observed 808.3968.

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

Procedure: A solution of 10 parts of 3β-acetoxy-6-(bromomethyl)cholest-5-ene and 20 parts of bis(ethoxyethyl)amine in 13 parts of dichloromethane is allowed to stand at room temperatures for 24 hours, whereupon 5 volumes of water is introduced and the oil which separates is extracted with diethyl ether. The extract is washed with water, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation to give 3β-acetoxy-6-[di(2-ethoxyethyl)aminomethyl]cholest-5-ene as the residue. The product, an oil, has the formula ##SPC9## is introduced the oil which separates is extracted with diethyl ether The extract is washed with water dried over anhydrous sodium sulfate stripped of solvent by vacuum distillation

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

Procedure: Bis-(2-ethoxyethyl)amine (560 μL, 3.13 mmol) was added to a solution of trimethylaluminum in toluene (1.56 mL, 3.13 mmol) and the solution was stirred for 20 minutes. A portion (424 μL) of the resulting solution was added to a solution of 7-chloro-3-(ethoxycarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione (100 mg, 0.313 mmol) in toluene (780 μL). The resulting solution was stirred for 4.5 hours at room temperature and then quenched with aqueous hydrochloric acid (1.5 mL, 1N) and water (20 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL) and the organic layers were concentrated on a rotary evaporator. The crude product was purified by flash chromatography eluting with chloroform:2-propanol (99:1-80:20) to give the title compound (60.8 mg, 45% yield, m.p. 202° C.). The resulting solution was stirred for 4.5 hours at room temperature quenched with aqueous hydrochloric acid (1.5 mL, 1N) and water (20 mL) The aqueous layer was extracted with ethyl acetate (3×50 mL) the organic layers were concentrated on a rotary evaporator The crude product was purified by flash chromatography eluting with chloroform:2-propanol (99:1-80:20)