1-Bromo-2-methylpropane → 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(4,6-dimethylpyrimidin-2-yl)-N-isobutylbenzenesulfonamide

HRID 594146Notes

Reaction equation

HRID 594146 reaction equation
[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[N:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[N:20]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:27])[O:4][N:3]=1.[C:28](N=C(N(C)C)N(C)C)([CH3:31])([CH3:30])[CH3:29].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[N:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[N:20]=3)[CH2:29][CH:28]([CH3:31])[CH3:30])(=[O:16])=[O:17])=[CH:11][CH:10]=2)=[C:5]([CH3:27])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 898760544-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide

Product 1

HCID 721960214-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(4,6-dimethylpyrimidin-2-yl)-N-isobutylbenzenesulfonamideYield 10.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (100 mg, 0.257 mmol) in acetonitrile (5 mL) stirred at room temperature, was added 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (0.054 mL, 0.257 mmol). The mixture was stirred at room temperature for 1 hour, then 1-bromo-2-methylpropane (0.056 mL, 0.515 mmol) added. The reaction was then heated by microwaves to 150° C., for 25 minutes. After cooling the solvent was removed under a stream of nitrogen and the crude sample purified by mass directed autoprep (formic acid modifier). The solvent was removed under a stream of nitrogen to give the title product (11.7 mg) as a yellow oil which solidified. LCMS (2 min, formic) Rt 1.31 min, m/z (ES+) 445 (M+H).

Workup

  1. temperatureThe reaction was then heated by microwaves to 150° C., for 25 minutes
  2. temperatureAfter cooling the solvent
  3. customwas removed under a stream of nitrogen
  4. customthe crude sample purified by mass
  5. customThe solvent was removed under a stream of nitrogen

Sources & evidence

ORD record
ord-a9f9e5cbb6a54b619be7886853468925
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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