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

HRID 1912462노트

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HRID 1912462 반응식
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]

참가 물질

5

반응물 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 45790144HCID 45790144, 화합물HCID 178418918HCID 178418918, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c804a1f3ad174e148d583fd412aaaabd
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609660B2

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