Water → 2-(5-Bromo-4-adamantanecarboxamido-6-oxopyridazin-1(6H)-yl)acetic acid

HRID 2092081Notes

Reaction equation

HRID 2092081 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([O:12]CC)=[O:11])[N:5]=[CH:4][C:3]=1[NH2:15].[H-].[Na+].[C:18]12([C:28](Cl)=[O:29])[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2.O>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([OH:12])=[O:11])[N:5]=[CH:4][C:3]=1[NH:15][C:28]([C:18]12[CH2:27][CH:22]3[CH2:21][CH:20]([CH2:26][CH:24]([CH2:23]3)[CH2:25]1)[CH2:19]2)=[O:29]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 989151-Adamantanecarbonyl chlorideHCID 59574360Ethyl 2-(5-bromo-4-amino-6-oxopyridazin-1(6H)-yl)acetate

Product 1

HCID 595746622-(5-Bromo-4-adamantanecarboxamido-6-oxopyridazin-1(6H)-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-(5-bromo-4-amino-6-oxopyridazin-1(6H)-yl)acetate (100 mg, 0.362 mmol) in tetrahydrofuran (2 mL) was mixed with sodium hydride (58 mg, 1.46 mmol) and adamantanecarbonyl chloride (144 mg, 0.724 mmol) at room temperature and stirred at room temperature for 30 minutes. After completion of the reaction, the reaction solution was mixed with water and ethyl acetate and extracted with 1 M aqueous sodium hydroxide. The aqueous layer was acidified to pH 1 with 1 M hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and the solvent was removed by distillation to give the desired product.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with 1 M aqueous sodium hydroxide
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-d8173639672744e98962b0c3549599af
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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