Triethylamine → N-methoxy-N,1-dimethyl-1H-pyrazole-4-carboxamide
Reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[N:3]1.Cl.[CH3:11][NH:12][O:13][CH3:14].Cl.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C>ClCCl.O>[CH3:14][O:13][N:12]([CH3:11])[C:7]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=1)=[O:9]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 13 °C
Procedure
A mixture of 1-methyl-1H-pyrazole-4-carboxylic acid (5.0 g, 39.6 mmol), N,O-dimethylhydroxylamine hydrochloride (4.8 g, 48.0 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (9.2 g, 48.0 mmol), hydroxybenzotriazole (6.5 g, 48.0 mmol) and triethylamine (12.1 g, 120 mmol) in dichloromethane (100 mL) was stirred at 9-17° C. overnight. The reaction mixture was diluted with water (50 mL) and the resulting mixture was extracted with EtOAc (30 mL×3), the combined organic layers were washed with brine (50 mL) and dried over anhydrous Na2SO4, filtered and concentrated in vacuo (an example of a standard aqueous/EtOAc procedure), then purified by silica gel column chromatography (PE:EtOAc=5:1) to give product (4.6 g, yield 69%).
Workup
- extractionthe resulting mixture was extracted with EtOAc (30 mL×3)
- washthe combined organic layers were washed with brine (50 mL)
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo (an example of a standard aqueous/EtOAc procedure),
- customthen purified by silica gel column chromatography (PE:EtOAc=5:1)
Sources & evidence
- ORD record
- ord-3cb3e3237b8a4ce9b9ad95b46acdf0fb
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946434B2
Reaction notes
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