Dabco → HCID 67958277, 화합물

HRID 2369593노트

반응식

HRID 2369593 반응식
N12CCN(CC1)CC2.[CH3:9][N:10]([CH3:15])[S:11](Cl)(=[O:13])=[O:12].[CH2:16]([O:18][C:19]([C:21]1[NH:22][N:23]=[C:24]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=1)=[O:20])[CH3:17]>CC#N.O>[CH2:16]([O:18][C:19]([C:21]1[N:22]([S:11](=[O:13])(=[O:12])[N:10]([CH3:15])[CH3:9])[N:23]=[C:24]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=1)=[O:20])[CH3:17]

참가 물질

6

반응물 3

HCID 9237DabcoHCID 83372Dimethylsulphamoyl chlorideHCID 178469067HCID 178469067, 화합물

생성물 1

HCID 67958277HCID 67958277, 화합물수율 84.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

1,4-Diazabicylo[2.2.2]octane (1.0 g, 8.93 mmol) and dimethylsulfamoyl chloride (0.88 mL, 8.2 mmol) were sequentially added to a solution of 5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (2.0 g, 8.12 mmol) in CH3CN (10 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 18 hours. The mixture was diluted with H2O and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents concentrated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 40/60). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (2.42 g, 84% yield) as a white solid.

후처리

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe solvents concentrated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 40/60)
  7. customThe desired fractions were collected
  8. customthe solvents evaporated in vacuo

출처 및 근거

ORD 기록
ord-e4a98de59dd349cca55479fdc0ce8560
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703946B2

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