1-Bromo-2-methylpropane → 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isobutyl-N-(5-methylpyridin-2-yl)benzenesulfonamide

HRID 594148

반응식

HRID 594148 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]([CH3:25])=[CH:21][N:20]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:26])[O:4][N:3]=1.[C:27](N=C(N(C)C)N(C)C)([CH3:30])([CH3:29])[CH3:28].BrCC(C)C>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]([CH2:28][CH:27]([CH3:30])[CH3:29])[C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)(=[O:17])=[O:16])=[CH:13][CH:14]=2)=[C:5]([CH3:26])[O:4][N:3]=1

참가 물질

5

반응물 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 898762704-((3,5-dimethylisoxazol-4-yl)-methoxy)-N-(5-methylpyridin-2-yl)benzenesulfonamide

생성물 1

HCID 721960224-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isobutyl-N-(5-methylpyridin-2-yl)benzenesulfonamide수율 4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(5-methylpyridin-2-yl)benzenesulfonamide (187 mg, 0.5 mmol) in acetonitrile (5 mL) stirred at room temperature, was added 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (0.261 mL, 1.250 mmol). The mixture was stirred at room temperature for 1 hour, then 1-bromo-2-methylpropane (0.190 mL, 1.750 mmol) added. The reaction was then heated by microwaves to 160° C., for 25 minutes. After cooling, dicholormethane (5 mL) was added to the mixture and the organic phase washed with water (5 mL) then separated using a hydrophobic frit. The solvent was removed under a stream of nitrogen and the crude sample purified by mass directed autoprep (ammonium carbonate modifier) to give the title product (8.5 mg). LCMS (3 min, High pH) Rt 1.88 min, m/z (ES+) 430 (M+H).

후처리

  1. temperatureThe reaction was then heated by microwaves to 160° C., for 25 minutes
  2. temperatureAfter cooling
  3. additiondicholormethane (5 mL) was added to the mixture
  4. washthe organic phase washed with water (5 mL)
  5. customthen separated
  6. customThe solvent was removed under a stream of nitrogen
  7. customthe crude sample purified by mass

출처 및 근거

ORD 기록
ord-84ca2019465b432baac42525ba1c3256
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242972B2

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