1-Bromo-2-methylpropane → HCID 72194823, compound

HRID 594171Notes

Reaction equation

HRID 594171 reaction equation
[CH:1]1([C:4]2[N:9]=[N:8][C:7]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]4[C:23]([CH3:28])=[N:24][O:25][C:26]=4[CH3:27])=[CH:16][CH:15]=3)(=[O:13])=[O:12])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[C:29](N=C(N(C)C)N(C)C)([CH3:32])([CH3:31])[CH3:30].BrCC(C)C>C(#N)C>[CH:1]1([C:4]2[N:9]=[N:8][C:7]([N:10]([CH2:30][CH:29]([CH3:32])[CH3:31])[S:11]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]4[C:23]([CH3:28])=[N:24][O:25][C:26]=4[CH3:27])=[CH:18][CH:19]=3)(=[O:12])=[O:13])=[CH:6][CH:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 89876238HCID 89876238, compound

Product 1

HCID 72194823HCID 72194823, compoundYield 4.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-(6-cyclopropylpyridazin-3-yl)-4-((3,5-dimethylisoxazol-4-yl)methoxy)benzenesulfonamide (51 mg, 0.127 mmol) in acetonitrile (0.1 mL) stirred at room temperature, was added 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (0.051 mL, 0.255 mmol). The mixture was stirred at room temperature for 1 hour, then 1-bromo-2-methylpropane (0.028 mL, 0.255 mmol) added. The reaction was then heated by microwaves to 150° C., for 30 minutes. After cooling the solvent was removed under a stream of nitrogen and the crude sample purified by mass directed autoprep (formic acid modifier) to give the title product (2.8 mg). LCMS (2 min, formic) Rt 1.21 min, m/z (ES+) 457 (M+H).

Workup

  1. temperatureThe reaction was then heated by microwaves to 150° C., for 30 minutes
  2. temperatureAfter cooling the solvent
  3. customwas removed under a stream of nitrogen
  4. customthe crude sample purified by mass

Sources & evidence

ORD record
ord-ff649c3f09bc409e9a3dae7965c65f8e
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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