Potassium Carbonate → 2,6-Difluoro-3-[3-(4-methoxyphenyl)-[1,2,4]thiadiazol-5-ylmethoxy]-benzamide

HRID 453100노트

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HRID 453100 반응식
Br[CH2:2][C:3]1[S:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:4]=1.[F:16][C:17]1[C:25]([OH:26])=[CH:24][CH:23]=[C:22]([F:27])[C:18]=1[C:19]([NH2:21])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:16][C:17]1[C:25]([O:26][CH2:2][C:3]2[S:7][N:6]=[C:5]([C:8]3[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=3)[N:4]=2)=[CH:24][CH:23]=[C:22]([F:27])[C:18]=1[C:19]([NH2:21])=[O:20]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 451201362,6-Difluoro-3-hydroxybenzamideHCID 595495215-Bromomethyl-3-(4-methoxyphenyl)-[1,2,4]thiadiazole

생성물 1

HCID 252311072,6-Difluoro-3-[3-(4-methoxyphenyl)-[1,2,4]thiadiazol-5-ylmethoxy]-benzamide수율 30%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
25 °C

실험 절차

To a solution of 5-bromomethyl-3-(4-methoxyphenyl)-[1,2,4]thiadiazole (0.048 g, 0.15 mmol) in DMF (2 ml) was added 2,6-difluoro-3-hydroxybenzamide (0.027 g, 0.15 mmol) and potassium carbonate (0.76 g, 0.55 mmol). The reaction mixture was stirred at 25° C. for 12 h under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), the reaction mixture was evaporated to dryness under vacuum, added 30 ml water and extracted with ethyl acetate (3×20 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified over silica gel (100-200 M, 50% EtOAc-Hexane) to get the desired product (0.011 g, 30%).

후처리

  1. customAfter the completion of the reaction (TLC monitoring)
  2. customthe reaction mixture was evaporated to dryness under vacuum
  3. additionadded 30 ml water
  4. extractionextracted with ethyl acetate (3×20 ml)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe crude residue was purified over silica gel (100-200 M, 50% EtOAc-Hexane)

출처 및 근거

ORD 기록
ord-3e4c7f56f18c4ccb8d3204e62967f375
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492414B2

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