Acetic Anhydride → Methyl 2-[5-acetamido-3-(3-pyridyl)pyrazol-1-yl]acetate

HRID 2205794Notes

Reaction equation

HRID 2205794 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[N:13]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[N:12]=[C:11]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:10]=1>N1C=CC=CC=1>[C:1]([NH:8][C:9]1[N:13]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[N:12]=[C:11]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86717291Methyl 2-[5-amino-3-(3-pyridyl)pyrazol-1-yl]acetate

Product 1

HCID 86717292Methyl 2-[5-acetamido-3-(3-pyridyl)pyrazol-1-yl]acetateYield 71.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (431 μL, 4.4 mmol) was added dropwise to a solution of methyl 2-[5-amino-3-(3-pyridyl)pyrazol-1-yl]acetate (510 mg, 2.2 mmol) in pyridine (1.7 mL) at 0° C. under an atmosphere of nitrogen. Upon complete addition, the reaction mixture was warmed to room temperature and stirred for 16 h. The reaction mixture was filtered and the solid was washed with diethyl ether to provide the title compound as a white solid (430 mg).

Workup

  1. additionUpon complete addition
  2. filtrationThe reaction mixture was filtered
  3. washthe solid was washed with diethyl ether

Sources & evidence

ORD record
ord-7c2eb639bfbd45288f8837f8d23139a3
Source dataset
uspto-grants-2016_06
Patent number
US09371332B2

Reaction notes

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