2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amide → 5-Acetyl-3-phenoxymethyl-pyrazole-1-sulfonic acid dimethylamide

HRID 2369595노트

반응식

HRID 2369595 반응식
[CH3:1][Mg]Br.CON(C)[C:7]([C:9]1[N:10]([S:22](=[O:27])(=[O:26])[N:23]([CH3:25])[CH3:24])[N:11]=[C:12]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]=1)=[O:8]>C1(C)C=CC=CC=1.C1COCC1.[NH4+].[Cl-]>[CH3:25][N:23]([CH3:24])[S:22]([N:10]1[C:9]([C:7](=[O:8])[CH3:1])=[CH:13][C:12]([CH2:14][O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:11]1)(=[O:26])=[O:27]

참가 물질

6

반응물 2

HCID 866738982-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amideHCID 178418573HCID 178418573, 화합물2회

생성물 1

HCID 679600925-Acetyl-3-phenoxymethyl-pyrazole-1-sulfonic acid dimethylamide수율 89%

시약·촉매·용매 3

HCID 1140Toluene용매2회HCID 8028Tetrahydrofuran용매3회HCID 25517Ammonium Chloride용매

반응 조건

온도
-78 °C

실험 절차

A 1.4M solution of methylmagnesium bromide in toluene and THF (3.88 mL, 5.43 mmol) was added to a solution of 2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amide (1.54 g, 4.17 mmol) in THF (20 mL) at −78° C. and under nitrogen. The mixture was stirred at −78° C. for 1 hour and then at room temperature for 16 hours. Then, a second portion of methylmagnesium bromide in toluene and THF (3.58 mL, 5.01 mmol) was added at 0° C. and the mixture was stirred at room temperature for 3 hours. The mixture was diluted with a saturated solution of NH4Cl and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 50/50). The desired fractions were collected and the solvents evaporated in vacuo to yield 5-acetyl-3-phenoxymethyl-pyrazole-1-sulfonic acid dimethylamide (1.2 g, 89% yield) as a white solid.

후처리

  1. waitat room temperature for 16 hours
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. extractionextracted with AcOEt
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvents evaporated in vacuo
  8. customThe crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 50/50)
  9. customThe desired fractions were collected
  10. customthe solvents evaporated in vacuo

출처 및 근거

ORD 기록
ord-8b14aa4a40ab49e9ac33ab5d891ff32b
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703946B2

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