Ethyl bromoacetate → HCID 68431289, compound

HRID 2092055Notes

Reaction equation

HRID 2092055 reaction equation
[Br:1][C:2]1[C:3](=[O:19])[NH:4][N:5]=[CH:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][C@@H:13]2[CH2:15][C@@H:11]([C:12]2([CH3:17])[CH3:16])[C@H:10]1[CH3:18].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[Br:1][C:2]1[C:3](=[O:19])[N:4]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:5]=[CH:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][C@@H:13]2[CH2:15][C@@H:11]([C:12]2([CH3:16])[CH3:17])[C@H:10]1[CH3:18]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 68429305HCID 68429305, compound

Product 1

HCID 68431289HCID 68431289, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Bromo-5-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-3(2H)-one (600 mg, 1.84 mmol) in N,N-dimethylformamide (6 mL) was mixed with ethyl bromoacetate (306 μL, 2.76 mmol) and potassium carbonate (381 mg, 2.76 mmol) at room temperature and stirred at 80° C. for 1.5 hours. After cooling, the reaction solution was mixed with saturated aqueous ammonium chloride and extracted with ethyl acetate. The resulting organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (chloroform/ethyl acetate=8/1) to give the desired product (670 mg, 88% yield).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe resulting organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (chloroform/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-a79528d8385c41c994c92cee533b13be
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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