Potassium Carbonate → HCID 68430621, compound

HRID 2092116Notes

Reaction equation

HRID 2092116 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[C:21]1([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[Br:1][C:2]1[C:3](=[O:19])[N:4]([C:21]2([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:24][CH2:23][CH2:22]2)[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 97595Ethyl 1-bromocyclobutanecarboxylateHCID 68429305HCID 68429305, compound

Product 1

HCID 68430621HCID 68430621, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

4-Bromo-5-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-3(2H)-one (112.8 mg, 0.35 mmol) in N,N-dimethylformamide (2 mL) was mixed with ethyl 1-bromocyclobutanecarboxylate (85.8 μL, 0.53 mmol) and potassium carbonate (73.0 mg, 0.53 mmol) at room temperature and stirred at 150° C. for 2 hours in a microwave reactor. After cooling, the reaction solution was mixed with saturated aqueous ammonium chloride and extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting crude product containing the desired product was used for the next reaction (222.1 mg).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. additionThe resulting crude product containing the desired product
  6. customwas used for the next reaction (222.1 mg)

Sources & evidence

ORD record
ord-6820a95097b544e6a077bb78a0e210cc
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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