4-[3-(dimethylamino)propoxy]benzaldehyde

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 stirred solution of 61.0 g (0.50 mole) of 4-hydroxybenzaldehyde in 400 ml of dimethylformamide (nitrogen atmosphere) is gradually treated with 24.0 g of 50% NaH. The temperature is kept below 35° using an ice water bath. When the addition is completed, the thick mixture is heated to 70° several minutes, then cooled to 35° before the addition of 417 ml of 1.8N (0.75 mole) of 3-dimethylaminopropyl chloride in toluene. is kept below 35° When the addition the thick mixture is heated to 70° several minutes

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

Procedure: A stirred solution of 61.0 g (0.50 mole) of 4-hydroxybenzaldehyde in 400 ml of dimethylformamide (nitrogen atmosphere) is gradually treated with 24.0 g of 50% NaH. The temperature is kept below 35° using an ice water bath. When the addition is completed, the thick mixture is heated to 70° several minutes, then cooled to 35° before the addition of 417 ml of 1.8N (0.75 mole) of 3-dimethylaminopropyl chloride in toluene. is kept below 35° When the addition the thick mixture is heated to 70° several minutes

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

Procedure: A stirred solution of 61.0 g (0.50 mole) of 4-hydroxybenzaldehyde in 400 ml of dimethylformamide (nitrogen atmosphere) is gradually treated with 24.0 g of 50% NaH. The temperature is kept below 35° using an ice water bath. When the addition is completed, the thick mixture is heated to 70° for several minutes, then cooled to 35° before the addition of 417 ml of 1.8N (0.75 mole) of 3-dimethylaminopropyl chloride in toluene. is kept below 35° When the addition the thick mixture is heated to 70° for several minutes

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

Procedure: A stirred solution of 61.0 g (0.50 mole) of 4-hydroxybenzaldehyde in 400 ml of dimethylformamide (nitrogen atmosphere) is gradually treated with 24.0 g of 50% NaH. The temperature is kept below 35° using an ice water bath. When the addition is completed, the thick mixture is heated to 70° for several minutes, then cooled to 35° before the addition of 417 ml of 1.8N (0.75 mole) of 3-dimethylaminopropyl chloride in toluene. is kept below 35° When the addition the thick mixture is heated to 70° for several minutes

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

Procedure: A stirred solution of 61.0 g (0.50 mole) of 4-hydroxybenzaldehyde in 400 ml of dimethylformamide (nitrogen atmosphere) is gradually treated with 24.0 g of 50% NaH. The temperature is kept below 35° using an ice water bath. When the addition is completed, the thick mixture is heated to 70° for several minutes, then cooled to 35° before the addition of 417 ml of 1.8N (0.75 mole) of 3-dimethylaminopropyl chloride in toluene. is kept below 35° When the addition the thick mixture is heated to 70° for several minutes

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

Procedure: A stirred solution of 61.0 g (0.50 mole) of 4-hydroxybenzaldehyde in 400 ml of dimethylformamide (nitrogen atmosphere) is gradually treated with 24.0 g of 50% NaH. The temperature is kept below 35° using an ice water bath. When the addition is completed, the thick mixture is heated to 70° for several minutes, then cooled to 35° before the addition of 417 ml of 1.8N (0.75 mole) of 3-dimethylaminopropyl chloride in toluene. is kept below 35° When the addition the thick mixture is heated to 70° for several minutes

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

Procedure: The compound was synthesized as trifluoroacetate salt starting from trimethyl silyl cyanide (1.88 mL, 20.72 mmol), 5-amino benzimidazole (0.82 g, 6.21 mmol), 4-(3-(dimethylamino)propoxy)benzaldehyde (1.0 g, 5.18 mmol), 10% Pd—C (250 mg), triethylamine (7.5 mL, 51.91 mmol), 1,1′-carbonyldiimidazole (1 g, 6.48 mmol). The product was further purified by prep HPLC using the following conditions: Column: Chiralpak AD-HMobile phase: Hexane:Ethanol (0.1% DEA); Flow rate: 32 mL/min, UV: 210 nm, Diluent: Mobile phase The prep fractions were concentrated in vacuum and partitioned between water and chloroform. The separated organic layer was washed with brine solution. Dried over anhydrous sodium sulphate and concentrated in vacuum to afford 50 mg of the product as brown solid. The product was further purified by prep HPLC Flow rate: 32 mL/min, UV: 210 nm, Diluent: Mobile phase The prep fractions were concentrated in vacuum partitioned between water and chloroform The separated organic layer was washed with brine solution Dried over anhydrous sodium sulphate concentrated in vacuum

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.03 g, 9.14 mmol), 4-[3-(dimethylamino)propoxy]benzaldehyde (2.76 ml), and xylenes was heated at 120° C. for 1 hour, then at 160° C. for 6 hours. p-Toluenesulfonic acid (300 mg) was added and the mixture was heated at 160° C. until the reaction was complete. The reaction mixture was cooled to room temperature, and a creamy white solid formed, which was collected by filtration, washed with methanol and recrystallized from ethyl acetate to afford 1-cyclopentyl-3-ethyl-6-[4-[3-(dimethylamino)propoxy]phenyl]pyrazolo[3,4-d]pyrimidin-4-one, as a white solid, m.p. 175-178° C. the mixture was heated at 160° C. until the reaction The reaction mixture was cooled to room temperature a creamy white solid formed which was collected by filtration washed with methanol recrystallized from ethyl acetate

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

Procedure: 4-(3-Dimethylaminopropoxy)benzaldehyde (30.0 g) is reacted with 18 g of phenethylamine in 150 ml of toluene as described under Example 1 to give 41 g of an oil; boiling point 184°-189° C/0.1-0.2 mm of Hg.

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

Procedure: The compound was synthesized as trifluoroacetate salt starting from trimethyl silyl cyanide (1.88 mL, 20.72 mmol), 5-amino benzimidazole (0.82 g, 6.21 mmol), 4-(3-(dimethylamino)propoxy)benzaldehyde (1.0 g, 5.18 mmol), 10% Pd—C (250 mg), triethylamine (7.5 mL, 51.91 mmol), 1,1′-carbonyldiimidazole (1 g, 6.48 mmol). The product was further purified by prep HPLC using the following conditions: Column: Chiralpak AD-HMobile phase: Hexane: Ethanol (0.1% DEA); Flow rate: 32 mL/min, UV: 210 nm, Diluent: Mobile phase The prep fractions were concentrated in vacuum and partitioned between water and chloroform. The separated organic layer was washed with brine solution. Dried over anhydrous sodium sulphate and concentrated in vacuum to afford 50 mg of the product as brown solid. The product was further purified by prep HPLC Flow rate: 32 mL/min, UV: 210 nm, Diluent: Mobile phase The prep fractions were concentrated in vacuum partitioned between water and chloroform The separated organic layer was washed with brine solution Dried over anhydrous sodium sulphate concentrated in vacuum