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

HRID 1912462ノート

反応式

HRID 1912462 の反応式
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]

参加物

5

反応物 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 45790144HCID 45790144、化合物HCID 178418918HCID 178418918、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c804a1f3ad174e148d583fd412aaaabd
出典データセット
uspto-grants-2013_12
特許番号
US08609660B2

反応ノート

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