Acetyl chloride → HCID 178474038, compound

To a solution of 3-(3-fluorophenyl)-1H-pyrazol-5-amine (6.5 g, 36 mmol) and N-methylmorpholine (9.7 mL, 88 mmol) in CH2Cl2 (150 mL) was added acetyl chloride (6 mL, 85 mmol) dropwise at 0° C. under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 1 d. The reaction mixture was concentrated in vacuo. MeOH (50 mL) and THF (50 mL) were added to the residue, followed by the addition of NaOH solution (aq. 2.5 M, 42.5 mL) at 0° C. The reaction mixture was stirred at room temperature for 15 min and HCl solution was added until pH reached ˜6. The organic solvents were evaporated in vacuo. The solid from the resulting aqueous suspension was collected by filtration, yielding the title compound as a solid (7.6 g).

1. concentrationThe reaction mixture was concentrated in vacuo
2. additionMeOH (50 mL) and THF (50 mL) were added to the residue
3. additionfollowed by the addition of NaOH solution (aq. 2.5 M, 42.5 mL) at 0° C
4. stirringThe reaction mixture was stirred at room temperature for 15 min
5. additionHCl solution was added until pH
6. customThe organic solvents were evaporated in vacuo
7. filtrationThe solid from the resulting aqueous suspension was collected by filtration

ORD record

ord-962ba44ff07f44a5a876dd62f68038b1

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371332B2