HCID 68873297, compound → HCID 58513576, compound

HRID 1817903Notes

Reaction equation

HRID 1817903 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:15][CH2:16][CH:17]2[CH2:19][CH2:18]2)=[C:6]([NH:8][C:9](=O)[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:15]([CH2:16][CH:17]3[CH2:19][CH2:18]3)[C:9]([C:10]([CH3:13])([CH3:12])[CH3:11])=[N:8][C:6]=2[CH:7]=1

Participants

3

Reactant 1

HCID 68873297HCID 68873297, compound

Product 1

HCID 58513576HCID 58513576, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-{5-bromo-2-[(cyclopropylmethyl)amino]phenyl}-2,2-dimethylpropanamide (step A, 1.41 g, 4.34 mmol) and p-toluenesulfonic acd monohydrate (825 mg, 4.34 mmol) in toluene (50 mL) was stirred at 120° C. for 20 h. After cooling to room temperature, the mixture was quenched with sodium hydrogencarbonate aqueous solution. The organic layer was separated. The aqueous layer was extracted with ethylacetate. The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1 as eluent) to afford the title compound (1.40 g, quantum yield) as a light brown oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was quenched with sodium hydrogencarbonate aqueous solution
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted with ethylacetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1 as eluent)

Sources & evidence

ORD record
ord-ba29aa0cfee24a04b990aa756a23d886
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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