Ethanol → HCID 70983988, compound

HRID 1775570Notes

Reaction equation

HRID 1775570 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:3]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21].C(O)C>N1C=CC=CC=1>[C:20]([NH:1][C:2]1[N:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:5]=[C:4]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[CH:3]=1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 702EthanolHCID 7918Acetic AnhydrideHCID 55170688HCID 55170688, compound

Product 1

HCID 70983988HCID 70983988, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of ethyl 2-(5-amino-3-(4-fluorophenyl)-1H-pyrazol-1-yl)acetate (6.91 g, 26.3 mmol) in pyridine (62 mL) was added acetic anhydride (3 ml, 31.5 mmol). The reaction was stirred at room temperature for 16 h. Ethanol was added and the mixture was concentrated in vacuo. The crude residue was purified by column chromatography (silica gel, gradient 10 to 100% ethyl acetate/isohexane) yielding ethyl 2-(5-acetamido-3-(4-fluorophenyl)-1H-pyrazol-1-yl)acetate as a solid (7.6 g).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe crude residue was purified by column chromatography (silica gel, gradient 10 to 100% ethyl acetate/isohexane)

Sources & evidence

ORD record
ord-1f8840ee513840e88ba59be882c4f2c5
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

Loading…