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A mixture of (2E)-3-(5-{[(3R)-1-cyclohexyl-3-piperidinyl]amino}-2-pyrazinyl)acrylic acid (209 mg), O-(tetrahydro-2H-pyran-2-yl)-hydroxylamine (89 mg), HOBt (111 μg) and EDCI (158 mg) in DMF (4.5 mL) was stirred at 0° C. for 1 hr and the mixture was stirred at ambient temperature for 18 hrs. The reaction mixture was evaporated in vacuo and the residue was partitioned between saturated sodium bicarbonate solution and EtOAc. The organic layer was separated, washed water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform-MeOH=95-5) to give (2E)-3-(5-{[(3R)-1-cyclohexyl-3-piperidinyl]amino}-2-pyrazinyl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (198 mg) as an amorphous powder.

1. stirringthe mixture was stirred at ambient temperature for 18 hrs
2. customThe reaction mixture was evaporated in vacuo
3. customthe residue was partitioned between saturated sodium bicarbonate solution and EtOAc
4. customThe organic layer was separated
5. washwashed water and brine
6. dry with materialdried over magnesium sulfate
7. customevaporated in vacuo
8. customThe residue was purified by silica gel column chromatography (chloroform-MeOH=95-5)