(1-benzylpyrrolidin-2-yl)methanamine

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 suspension of 4.0 g of methyl 2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylate and 3.37 g of 1-benzyl-2-aminomethyl-pyrrolidine in 15 ml of diethylene glycol is heated at 120°-130° C. and stirred for 30-31 hours. The reaction solution is cooled to room temperature, poured into 150-200 ml of water, and extracted with ethyl acetate three times. The ethyl acetate extract is washed with water followed by sodium chloride saturated water. The product is dried over magnesium sulfate and the solvent is distilled off under diminished pressure. The resulting residue is recrystallized from isopropanol by the use of decolorizing charcoal to give crystals of N-(1-benzyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide, m.p. 161°-167° C. is heated at 120°-130° C. extracted with ethyl acetate three times The ethyl acetate extract is washed with water The product is dried over magnesium sulfate the solvent is distilled off under diminished pressure The resulting residue is recrystallized from isopropanol by the use of decolorizing charcoal

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

Procedure: A suspension of 4.0 g of methyl 2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylate and 3.37 g of 1-benzyl-2-aminomethyl-pyrrolidine in 15 ml of diethylene glycol is heated at 120°-130° C. and stirred for 30-31 hours. The reaction solution is cooled to room temperature, poured into 150-200 ml of water, and extracted with ethyl acetate three times. The ethyl acetate extract is washed with water followed by sodium chloride saturated water. The product is dried over magnesium sulfate and the solvent is distilled off under diminished pressure. The resulting residue is recrystallized from isopropanol by the use of decolorizing charcoal to give crystals of N-(1-benzyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide, m.p. 161°-167° C. is heated at 120°-130° C. extracted with ethyl acetate three times The ethyl acetate extract is washed with water The product is dried over magnesium sulfate the solvent is distilled off under diminished pressure The resulting residue is recrystallized from isopropanol by the use of decolorizing charcoal

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 25 mg of 4-benzylamino-6-chloropyridine-3-carboxyamide (the compound of Example 1) was dissolved in 0.5 ml of toluene, to which 13.5 mg of 4-aminopyridine, 2 mg of palladium (II) acetate, 248 mg of potassium carbonate and 11 mg of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl were added, and stirred at 100° C. for 28 hours. After cooling, the insoluble substances were filtered off, the filtered product was washed with toluene, combined with the filtrate, and the solvent was evaporated. The residue obtained was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain 4.8 mg (yield 16%) of the title compound as a slight yellow crystalline powder. were added After cooling the insoluble substances were filtered off the filtered product was washed with toluene the solvent was evaporated The residue obtained was purified by silica gel column chromatography (chloroform:methanol=10:1)

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

Procedure: 668.5 mg of the 2-azidomethyl-1-benzylpyrrolidine crude product obtained was dissolved in 5 mL of ethanol, to which 160 mg of 10% palladium carbon was added, and stirred at room temperature under an atmosphere of hydrogen gas for 5 hours. The 10% palladium carbon was celite-filtered, and the filtered product was washed with methanol. The solvent was evaporated, and the residue was purified by silica gel chromatography (chloroform to chloroform:methanol=30:1 to chloroform:methanol=15:1) to obtain 539.7 mg of the title compound crude product as a light yellow oil. Without further purification, this was used as the feed material for the next reaction. was added The 10% palladium carbon was celite-filtered the filtered product was washed with methanol The solvent was evaporated the residue was purified by silica gel chromatography (chloroform to chloroform:methanol=30:1 to chloroform:methanol=15:1)