1-dimethylsulfamoyl-1H-pyrazole-3-carboxylic acid methoxy-methyl-amide → 3-(3-chloro-benzoyl)-1H-pyrazole-1-sulfonic acid dimethylamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][CH:7]=1.CON(C)[C:13]([C:15]1[CH:19]=[CH:18][N:17]([S:20](=[O:25])(=[O:24])[N:21]([CH3:23])[CH3:22])[N:16]=1)=[O:14]>C1COCC1>[CH3:22][N:21]([CH3:23])[S:20]([N:17]1[CH:18]=[CH:19][C:15]([C:13](=[O:14])[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[N:16]1)(=[O:24])=[O:25]Participants
Conditions
- Temperature
- -78 °C
Procedure
A solution of 3-chlorophenylmagnesium bromide (0.5 M in THF) (15.89 mL, 7.95 mmol) was added to a solution of 1-dimethylsulfamoyl-1H-pyrazole-3-carboxylic acid methoxy-methyl-amide (1.60 g, 6.11 mmol) in THF (20 mL) at −78° C. and under nitrogen. The mixture was stirred at −78° C. for 1 hour and then further stirred at room temperature for 5 hours. The mixture was quenched with NH4Cl (aq. sat. solution) and the product was extracted with AcOEt. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 10/90). The desired fractions were collected and concentrated in vacuo to yield 3-(3-chloro-benzoyl)-1H-pyrazole-1-sulfonic acid dimethylamide (1.68 g, 88% yield) as a pale yellow solid.
Workup
- stirringfurther stirred at room temperature for 5 hours
- customThe mixture was quenched with NH4Cl (aq. sat. solution)
- extractionthe product was extracted with AcOEt
- customThe organic layer was separated
- dry with materialdried (MgSO4)
- filtrationfiltered
- customthe solvents evaporated in vacuo
- customThe crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 10/90)
- customThe desired fractions were collected
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-80c78cab9e7b4220be57377555c88efe
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609660B2
Reaction notes
Loading…