Methanamine, N-methoxy-, hydrochloride (1:1) → 1-dimethylsulfamoyl-1H-pyrazole-3-carboxylic acid methoxy-methyl-amide

HRID 1912462Notes

Reaction equation

HRID 1912462 reaction equation
CO[C:3]([C:5]1[CH:9]=[CH:8][N:7]([S:10](=[O:15])(=[O:14])[N:11]([CH3:13])[CH3:12])[N:6]=1)=[O:4].Cl.[CH3:17][NH:18][O:19][CH3:20].C([Mg]Cl)(C)C>C(Cl)Cl>[CH3:20][O:19][N:18]([CH3:17])[C:3]([C:5]1[CH:9]=[CH:8][N:7]([S:10](=[O:14])(=[O:15])[N:11]([CH3:12])[CH3:13])[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 45790144HCID 45790144, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 866908071-dimethylsulfamoyl-1H-pyrazole-3-carboxylic acid methoxy-methyl-amideYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

1-Dimethylsulfamoyl-1H-pyrazole-3-carboxylic acid methyl ester (4 g, 17.15 mmol) and N,O-dimethylhydroxylamine hydrochloride (2.18 g, 22.29 mmol) were slurried in DCM (20 mL). The mixture was flushed with nitrogen and cooled to −78° C. Then a solution of isopropylmagnesium chloride (2M in THF) (24.01 mL, 48.02 mmol) was added dropwise. When the addition was completed the mixture was allowed to warm to room temperature and stirred overnight. 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 100/0). The desired fractions were collected and concentrated in vacuo to yield 1-dimethylsulfamoyl-1H-pyrazole-3-carboxylic acid methoxy-methyl-amide (3.2 g, 71% yield) as a pale yellow oil.

Workup

  1. customThe mixture was flushed with nitrogen
  2. additionWhen the addition
  3. temperatureto warm to room temperature
  4. customThe mixture was quenched with NH4Cl (aq. sat. solution)
  5. extractionthe product was extracted with AcOEt
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvents evaporated in vacuo
  10. customThe crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 100/0)
  11. customThe desired fractions were collected
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c804a1f3ad174e148d583fd412aaaabd
Source dataset
uspto-grants-2013_12
Patent number
US08609660B2

Reaction notes

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