1-Bromo-2-methylpropane → HCID 72194694, compound

HRID 594167Notes

Reaction equation

HRID 594167 reaction equation
[CH:1]1([C:4]2[N:9]=[CH: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][N: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.O>[CH:1]1([C:4]2[N:9]=[CH: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][N:5]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 89875971HCID 89875971, compound

Product 1

HCID 72194694HCID 72194694, compoundYield 51.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of N-(2-cyclopropylpyrimidin-5-yl)-4-((3,5-dimethylisoxazol-4-yl)methoxy)benzenesulfonamide (74 mg, 0.185 mmol) in acetonitrile (0.1 mL) stirred at room temperature, was added 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (0.074 mL, 0.370 mmol). The mixture was stirred at room temperature for 1 hour, then 1-bromo-2-methylpropane (0.04 mL, 0.370 mmol) added. The reaction was then heated by microwaves to 150° C., for 30 minutes. After cooling the reaction was diluted with acetonitrile (0.5 mL) and water (0.5 mL) and the crude sample purified by mass directed autoprep (formic acid modifier) to give the title product (43.75 mg). LCMS (2 min, High pH) Rt 1.27 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 reaction
  3. customthe crude sample purified by mass

Sources & evidence

ORD record
ord-be472d447e864298a55d41443e558a58
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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