1-Bromo-2-methylpropane → 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-(3,5-dimethyl-2-pyridinyl)-N-(2-methylpropyl)benzenesulfonamide

HRID 594150

반응식

HRID 594150 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[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][N:20]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:27])[O:4][N:3]=1.[CH3:28][C:29](N=C(N(C)C)N(C)C)([CH3:31])[CH3:30].BrCC(C)C>C(#N)C>[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]([C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][N:20]=3)[CH2:28][CH:29]([CH3:31])[CH3:30])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:27])[O:4][N:3]=1

참가 물질

5

반응물 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 898763854-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-(3,5-dimethyl-2-pyridinyl)benzenesulfonamide

생성물 1

HCID 721941374-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-(3,5-dimethyl-2-pyridinyl)-N-(2-methylpropyl)benzenesulfonamide수율 46.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-(3,5-dimethyl-2-pyridinyl)benzenesulfonamide (56 mg, 0.145 mmol) in acetonitrile (1 mL) was added N″-(1,1-dimethylethyl)-N,N,N′,N′-tetramethylguanidine (25 mg, 0.145 mmol) and the mixture was stirred at room temperature for 1 hour, 1-bromo-2-methylpropane (0.031 mL, 0.289 mmol) was then added and the mixture was stirred at 70° C. for 125 hours. The mixture was concentrated in vacuo and partitioned between dichloromethane (5 mL) and water (5 mL). The organic layer was then purified by mass directed autoprep (formic acid modifier) to give the title compound (30 mg) as a white solid. LCMS (2 min, formic) Rt 1.31 min, m/z (ES+) 444 (M+H).

후처리

  1. stirringthe mixture was stirred at 70° C. for 125 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. custompartitioned between dichloromethane (5 mL) and water (5 mL)
  4. customThe organic layer was then purified by mass

출처 및 근거

ORD 기록
ord-c2bc17e51b0d4e6f8d5cbd9ffc9d4aa7
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242972B2

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