Potassium Carbonate → HCID 68431879, compound

HRID 2092058Notes

Reaction equation

HRID 2092058 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][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].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][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[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 68320Ethyl 3-bromopropionateHCID 68429305HCID 68429305, compound

Product 1

HCID 68431879HCID 68431879, compoundYield 166.8%

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 (320 mg, 0.637 mmol) in N,N-dimethylformamide (3.2 mL) was mixed with ethyl 3-bromopropionate (0.187 mL, 1.47 mmol) and potassium carbonate (244 mg, 1.76 mmol) at room temperature and stirred at 80° C. for 4 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 (453 mg, quant.).

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-3f02df8a3b3149a78a0e96b293f3e351
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

Loading…