2-(2-chlorophenoxy)ethanamine

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

Procedure: Compound C (200 mg, 589 mmol), 2-(2-chlorophenoxy)ethylamine (202 μl) and sodium hydrogencarbonate (495 mg) were added to DMSO (6 ml), and the mixture was stirred at 100° C. for 27 hr. After stirring, the reaction mixture was added to cold water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and concentrated, and the residue was washed by suspending in ethyl acetate. This was converted to hydrochloride to give the object compound of 2-(2-(2-chlorophenoxy)ethylamino)-6-(5-methyl-1H-pyrazol-3-ylamino)-4-(4-methoxyphenyl)nicotinonitrile hydrochloride (12 mg). After stirring the mixture was extracted with ethyl acetate The organic layer was washed with saturated brine concentrated the residue was washed

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

Procedure: Compound A (200 mg, 813 μmol), 2-(2-chlorophenoxy)ethylamine (280 μl) and sodium hydrogencarbonate (683 mg) were added to DMSO (6 ml), and the mixture was stirred at 100° C. for 27 hr. After stirring, the reaction mixture was added to cold water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and concentrated, and the residue was washed by suspending in ethyl acetate. This was converted to hydrochloride to give the object compound of 2-(2-(2-chlorophenoxy)ethylamino)-6-(5-methyl-1H-pyrazol-3-ylamino)-4-methylnicotinonitrile hydrochloride (18 mg). After stirring the mixture was extracted with ethyl acetate The organic layer was washed with saturated brine concentrated the residue was washed

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

Procedure: 21.0 grams (0.071 ml) of N-[2-(2-chlorophenoxy)ethyl]phthalimide and 3.55 grams (0.071 mol) of hydrazine hydrate are dissolved in 70 ml of moisture-free alcohol for heating and diffusing over 45 minutes. And stirred with 20 ml 18% HCl heat for diffusing over 1.0 hour. Upon cooling, after filtrating the extracted solids, 20% NaOH is added to alkalize. The mixed solution's organic layer is extracted with chloroform and filtrating the extracted solids with potassium carbonate solution. The generated product is filled into silica gel columns utilizing the ratio of ethyl acetate as the diluent; upon purification, 2-(2-chlorophenoxy) ethylamine is obtained. for heating heat for diffusing over 1.0 hour Upon cooling after filtrating the extracted solids, 20% NaOH is added The mixed solution's organic layer is extracted with chloroform filtrating the extracted solids with potassium carbonate solution The generated product is filled into silica gel columns upon purification