1-Bromo-3-methylbutane → 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isopentyl-N-(5-isopropylpyridin-2-yl)benzenesulfonamide

HRID 594164

반응식

HRID 594164 반응식
[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][N:20]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:28])[O:4][N:3]=1.C(N=C(N(C)C)N(C)C)(C)(C)C.Br[CH2:42][CH2:43][CH:44]([CH3:46])[CH3:45]>C(#N)C>[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([S:15]([N:18]([CH2:42][CH2:43][CH:44]([CH3:46])[CH3:45])[C:19]3[CH:24]=[CH:23][C:22]([CH:25]([CH3:26])[CH3:27])=[CH:21][N:20]=3)(=[O:17])=[O:16])=[CH:13][CH:14]=2)=[C:5]([CH3:28])[O:4][N:3]=1

참가 물질

5

반응물 3

HCID 78911-Bromo-3-methylbutaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 898760154-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(5-isopropylpyridin-2-yl)benzenesulfonamide

생성물 1

HCID 721946914-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isopentyl-N-(5-isopropylpyridin-2-yl)benzenesulfonamide수율 27.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
20 °C

실험 절차

To a stirred solution of 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(5-isopropylpyridin-2-yl)benzenesulfonamide (150 mg, 0.37 mmol) in acetonitrile (4 mL) was added 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (128 mg, 0.75 mmol). The reaction mixture was stirred at 20° C. for 1 hour. 1-Bromo-3-methylbutane (0.09 mL, 0.75 mmol) was then added and the reaction vessel sealed and heated by microwaves to 150° C. for 30 minutes. The reaction mixture was concentrated in vacuo and diluted with ethyl acetate. The organic phase was washed with water, dried using a hydrophobic frit and evaporated in vacuo to give the crude product. The crude was then purified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give the title compound (48 mg) as a yellow oil. LCMS (2 min, HpH) Rt 1.50 min, m/z (ES+) 472 (M+H).

후처리

  1. customthe reaction vessel sealed
  2. temperatureheated by microwaves to 150° C. for 30 minutes
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washThe organic phase was washed with water
  6. customdried
  7. customevaporated in vacuo
  8. customto give the crude product
  9. customThe crude was then purified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient)
  10. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-6d5bfe80f5e349348e559bcd410ba2ae
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242972B2

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