Pyridine-2-carboximidamide hydrochloride

White solid

Compound 1 (26.01) was stirred with sodium methoxide solution at room temperature for 22 hours, then ammonium chloride (28-01) was added for 6 hours, and unreacted ammonium chloride was removed by filtration, The filtrate was spin-dried to remove the methanol solvent to give a pale yellow solid powder which was then washed three times with diethyl ether to remove unreacted compound 1 and recrystallized from a mixed solvent of ethanol-ether to give compound 2 as a white product. Yield: 83percent.Prepare fresh sodium methoxide solution in a single mouth bottle, anhydrous methanol 20 mL asolution of 50 mg of sodium wire was added with stirring and the mixture was allowed to react completely with sodium, followed by 2-cyanopyridine (2.67 g, 26 mmol) and stirred at room temperature for 22 hours to form a homogeneous solution. After addition of ammonium chloride (1.1 g, 28 mmol), stirring was continued at room temperature for 6 hours. The unreacted ammonium chloride was removed by filtration and the filtrate was spin dried to remove the methanol solvent to give a pale yellow solid which was washed three times with ether to remove unreacted 2-cyanopyridine and recrystallized from ethanol-diethyl ether to give the product Py-NH2 as a white product. Yield: 83percent. Synthesis of 10-1Step A: Picolinamidine hydrochloride (10-b)To a solution of 2-cyanopyridine (10-a) (Sigma-Aldrich) (lOOg, 0.95mol) in methanol (1.5L) under nitrogen was added sodium methoxide (2.5g, 44mmol). The reaction mixture was stirred at room temperature for 24 hours. Ammonium chloride (53.5g, lmol) was added to the reaction mixture. The mixture was stirred at room temperature for 4h and the solvent was removed in vacuo. The residue was washed with ipropanol/ethyl acetate=l/10 and dried in vacuo to provide compound 10-b (lOOg, 66percent).SSSBLAI Pfco)in3/4mjdSodium methoxide (2.5g, 44mmol) was added to a solution of 2-cyanopyridine (lOOg, 0.95mol) in methanol (1.5L) under nitrogen. The reaction mixture was stirred at room temperature for 24 hours. Then ammonium chloride (53.5g, lmol) was added. The mixture was stirred at room temperature for 4h and the solvent was removed in vacuo. The residue was washed with ipropanol/ethyl acetate=l/10 and dried in vacuo to provide the product, 1-1-g, (100g, 66percent).Step D: Picolinamidine hydrochloride (1-1-g) Sodium methoxide (2.5g, 44mmol) was added to a solution of 2-cyanopyridine (1 OOg, 0.95mol) in methanol (1.5L) under nitrogen. The reaction mixture was stirred at room temperature for 24 hours. Then ammonium chloride (53.5g, lmol) was added. The mixture was stirred at room temperature for 4h and the solvent was removed in vacuo. The residue was washed with ipropanol/ethyl acetate=l/10 and dried in vacuo to provide the product, 1-1-g, (lOOg, 66percent).EXAMPLE 27 A mixture of 2-cyanopyridine (3.15 g, 30.3 mmol) and NaOCH3 (0.16 g, 3 mmol) is prepared in 10 mL ethanol and stirred at RT for 4 h under inert atmosphere. After 4 h, NH 4CI (1.81 g, 33.8 mmol) is added to the solution. The mixture is refluxed for 6 hours, cooled down and filtered to remove excess salt. Ethanol is removed and a white solid of 2-pyridinecarboximidamide hydrochloride (3.99 g, 25.2 mmol) is obtained.

Molecular Weight:157.60
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:157.0406750
Monoisotopic Mass:157.0406750
Topological Polar Surface Area:62.8
Heavy Atom Count:10
Complexity:111
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes