Potassium Carbonate → HCID 68431536, compound

HRID 2092064Notes

Reaction equation

HRID 2092064 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[CH:21]([CH3:27])[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]([CH:21]([CH3:27])[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 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 79040Ethyl 2-bromopropionateHCID 68429305HCID 68429305, compound

Product 1

HCID 68431536HCID 68431536, compoundYield 55%

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 (208 mg, 0.637 mmol) in N,N-dimethylformamide (2 mL) was mixed with ethyl 2-bromopropionate (124 μL, 0.955 mmol) and potassium carbonate (132 mg, 0.955 mmol) at room temperature and stirred at 80° C. for 2 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 to give the desired product (149 mg, 55% 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

Sources & evidence

ORD record
ord-9e47e11fc5fa45de9aff5b1c0bf082ec
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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