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

HRID 588592Notes

Reaction equation

HRID 588592 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 86717291HCID 86717291, compound

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-1cee3b9b3d5d4ef6a26a29876c158321
Source dataset
uspto-grants-2016_01
Patent number
US09227976B2

Reaction notes

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