N,N-二乙基-3-异硫氰酸丙烷-1-胺

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 200 mg (0.59 mmol) of 5-cyano-6-(2-fluoro-4-methoxyphenyl)-4-methyl-1H-pyrazolo[3,4-b]pyridine-3-carbohydrazide diluted in 8 ml of dimethylacetamide, are added 101 mg of N,N-diethyl-3-isothiocyanatopropane-1-amine. The reaction mixture is stirred at 65° C. until complete disappearance of the starting product. 224 mg (1.17 mmol) of N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride are added and the solution is stirred at 70° C. for 2 h. 20 ml of water are added and the product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, and concentrated. The solid is triturated in a diethyl ether/methanol mixture (10:1) to yield 170 mg of 3-(5-(3-(diethylamino)propylamino)-1,3,4-oxadiazol-2-yl)-6-(2-fluoro-4-methoxyphenyl)-4-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile in the form of a pink solid. the solution is stirred at 70° C. for 2 h the product is extracted several times with ethyl acetate dried over magnesium sulfate concentrated The solid is triturated in a diethyl ether/methanol mixture (10:1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 5.0 g (0.022 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine and 4.30 g (0.025 mole) of 3-(N,N-diethylamino)propylisothiocyanate in 400 ml of acetonitrile was refluxed for 16 hr. The solvent was removed in vacuo and the residue was dissolved in ether. The solution was extracted with three portions of water and was dried over magnesium sulfate. The volume of the ether solution was reduced to 200 ml, and hexane was added until the solution became slightly cloudy. A white solid precipitated to give 6.76 g (76.9%) of white crystalline solid, m.p. 120°-121° C. The solvent was removed in vacuo the residue was dissolved in ether The solution was extracted with three portions of water was dried over magnesium sulfate was added until the solution A white solid precipitated

反应条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 200 mg (0.59 mmol) of 5-cyano-6-(2-fluoro-4-methoxyphenyl)-4-methyl-1H-pyrazolo[3,4-b]pyridine-3-carbohydrazide diluted in 8 ml of dimethylacetamide, are added 101 mg of N,N-diethyl-3-isothiocyanatopropane-1-amine. The reaction mixture is stirred at 65° C. until complete disappearance of the starting product. 224 mg (1.17 mmol) of N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride are added and the solution is stirred at 70° C. for 2 h. 20 ml of water are added and the product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, and concentrated. The solid is triturated in a diethyl ether/methanol mixture (10:1) to yield 170 mg of 3-(5-(3-(diethylamino)propylamino)-1,3,4-oxadiazol-2-yl)-6-(2-fluoro-4-methoxyphenyl)-4-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile in the form of a pink solid. the solution is stirred at 70° C. for 2 h the product is extracted several times with ethyl acetate dried over magnesium sulfate concentrated The solid is triturated in a diethyl ether/methanol mixture (10:1)

反应条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 200 mg (0.59 mmol) of 5-cyano-6-(2-fluoro-4-methoxyphenyl)-4-methyl-1H-pyrazolo[3,4-b]pyridine-3-carbohydrazide diluted in 8 ml of dimethylacetamide, are added 101 mg of N,N-diethyl-3-isothiocyanatopropane-1-amine. The reaction mixture is stirred at 65° C. until complete disappearance of the starting product. 224 mg (1.17 mmol) of N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride are added and the solution is stirred at 70° C. for 2 h. 20 ml of water are added and the product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, and concentrated. The solid is triturated in a diethyl ether/methanol mixture (10:1) to yield 170 mg of 3-(5-(3-(diethylamino)propylamino)-1,3,4-oxadiazol-2-yl)-6-(2-fluoro-4-methoxyphenyl)-4-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile in the form of a pink solid. the solution is stirred at 70° C. for 2 h the product is extracted several times with ethyl acetate dried over magnesium sulfate concentrated The solid is triturated in a diethyl ether/methanol mixture (10:1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 5.0 g (0.022 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine and 4.30 g (0.025 mole) of 3-(N,N-diethylamino)propylisothiocyanate in 400 ml of acetonitrile was refluxed for 16 hr. The solvent was removed in vacuo and the residue was dissolved in ether. The solution was extracted with three portions of water and was dried over magnesium sulfate. The volume of the ether solution was reduced to 200 ml, and hexane was added until the solution became slightly cloudy. A white solid precipitated to give 6.76 g (76.9%) of white crystalline solid, m.p. 120°-121° C. The solvent was removed in vacuo the residue was dissolved in ether The solution was extracted with three portions of water was dried over magnesium sulfate was added until the solution A white solid precipitated

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 5.0 g (0.022 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine and 4.30 g (0.025 mole) of 3-(N,N-diethylamino)propylisothiocyanate in 400 ml of acetonitrile was refluxed for 16 hr. The solvent was removed in vacuo and the residue was dissolved in ether. The solution was extracted with three portions of water and was dried over magnesium sulfate. The volume of the ether solution was reduced to 200 ml, and hexane was added until the solution became slightly cloudy. A white solid precipitated to give 6.76 g (76.9%) of white crystalline solid, m.p. 120°-121° C. The solvent was removed in vacuo the residue was dissolved in ether The solution was extracted with three portions of water was dried over magnesium sulfate was added until the solution A white solid precipitated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 5.0 g (0.022 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine and 4.30 g (0.025 mole) of 3-(N,N-diethylamino)propylisothiocyanate in 400 ml of acetonitrile was refluxed for 16 hr. The solvent was removed in vacuo and the residue was dissolved in ether. The solution was extracted with three portions of water and was dried over magnesium sulfate. The volume of the ether solution was reduced to 200 ml, and hexane was added until the solution became slightly cloudy. A white solid precipitated to give 6.76 g (76.9%) of white crystalline solid, m.p. 120°-121° C. The solvent was removed in vacuo the residue was dissolved in ether The solution was extracted with three portions of water was dried over magnesium sulfate was added until the solution A white solid precipitated

反应条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 200 mg (0.59 mmol) of 5-cyano-6-(2-fluoro-4-methoxyphenyl)-4-methyl-1H-pyrazolo[3,4-b]pyridine-3-carbohydrazide diluted in 8 ml of dimethylacetamide, are added 101 mg of N,N-diethyl-3-isothiocyanatopropane-1-amine. The reaction mixture is stirred at 65° C. until complete disappearance of the starting product. 224 mg (1.17 mmol) of N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride are added and the solution is stirred at 70° C. for 2 h. 20 ml of water are added and the product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, and concentrated. The solid is triturated in a diethyl ether/methanol mixture (10:1) to yield 170 mg of 3-(5-(3-(diethylamino)propylamino)-1,3,4-oxadiazol-2-yl)-6-(2-fluoro-4-methoxyphenyl)-4-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile in the form of a pink solid. the solution is stirred at 70° C. for 2 h the product is extracted several times with ethyl acetate dried over magnesium sulfate concentrated The solid is triturated in a diethyl ether/methanol mixture (10:1)

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 5.0 g (0.022 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine and 4.30 g (0.025 mole) of 3-(N,N-diethylamino)propylisothiocyanate in 400 ml of acetonitrile was refluxed for 16 hr. The solvent was removed in vacuo and the residue was dissolved in ether. The solution was extracted with three portions of water and was dried over magnesium sulfate. The volume of the ether solution was reduced to 200 ml, and hexane was added until the solution became slightly cloudy. A white solid precipitated to give 6.76 g (76.9%) of white crystalline solid, m.p. 120°-121° C. The solvent was removed in vacuo the residue was dissolved in ether The solution was extracted with three portions of water was dried over magnesium sulfate was added until the solution A white solid precipitated