Sodium Bicarbonate → HCID 90224873, compound

HRID 1487101Notes

Reaction equation

HRID 1487101 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:10]2([C:13]([OH:15])=O)[CH2:12][CH2:11]2)=[CH:4][C:3]=1[CH3:16].[O-:17][C:18]#[N:19].[K+].C(=O)([O-])O.[Na+]>C(O)(=O)C.ClCCl>[Br:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]([N:9]2[C:18](=[O:17])[NH:19][C:13](=[O:15])[C:10]32[CH2:11][CH2:12]3)=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 11378442Potassium cyanateHCID 90224845HCID 90224845, compound

Product 1

HCID 90224873HCID 90224873, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-((4-bromo-3,5-dimethylphenyl)amino)cyclopropane carboxylic acid (198 mg, 0.697 mmol) in acetic acid (3 mL) and dichloromethane (1.5 mL), potassium cyanate (424 mg, 5.23 mmol) was added at room temperature. The mixture was stirred at room temperature for one hour, and then stirred at 60° C. for two hours. A saturated aqueous sodium hydrogen carbonate solution was added to adjust pH to 8, and this mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-hexane) to afford 4-(4-bromo-3,5-dimethylphenyl)-4,6-diazaspiro[2.4]heptane-5,7-dione (49 mg, 23%).

Workup

  1. additionwas added at room temperature
  2. stirringstirred at 60° C. for two hours
  3. extractionthis mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-bfa530b6b444470a9b58ce8d678a25c8
Source dataset
uspto-grants-2016_08
Patent number
US09428505B2

Reaction notes

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