Potassium Carbonate → HCID 68432192, compound

HRID 2092061Notes

Reaction equation

HRID 2092061 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][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].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][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[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 76300Ethyl 4-bromobutyrateHCID 68429305HCID 68429305, compound

Product 1

HCID 68432192HCID 68432192, compoundYield 149.8%

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 (224 mg, 0.688 mmol) in N,N-dimethylformamide (2.2 mL) was mixed with ethyl 4-bromobutyrate (0.148 mL, 1.03 mmol) and potassium carbonate (142 mg, 1.03 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 (454 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-c3c89577a2354282aabbe01353806130
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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