61-16-5 → HCID 86647511, compound

HRID 2092088Notes

Reaction equation

HRID 2092088 reaction equation
[Br:1][C:2]1[C:3](=[O:33])[N:4]([CH2:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:24][CH:23]=2)=O)[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].CC([NH2:48])C(O)C1C=C(OC)C=CC=1OC.Cl.C([O:53][CH2:54]C)(=O)C>C(O)C>[Br:1][C:2]1[C:3](=[O:33])[N:4]([CH2:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([N:28]([CH2:29][CH3:30])[CH2:31][CH3:32])=[CH:24][CH:23]=2)=[N:48][O:53][CH3:54])[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]

Participants

5

Reactant 3

HCID 608161-16-5HCID 8857Ethyl AcetateHCID 68429113HCID 68429113, compound

Product 1

HCID 86647511HCID 86647511, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Bromo-2-{2-[4-(diethylamino)phenyl]-2-oxoethyl}-5-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-3(2H)-one (50 mg, 0.097 mmol) and methoxamine hydrochloride (41 mg, 0.485 mmol) in ethanol (0.5 mL) were stirred at 80° C. for 1 hour. After cooling, ethyl acetate was added, and the organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent was removed by distillation. The resulting residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1) to give the desired product (56 mg, 100% yield).

Workup

  1. temperatureAfter cooling
  2. washthe organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation
  5. customThe resulting residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-2ad90a7994824b5492b29f02010af3a8
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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