Hydrochloric Acid → 1-Cyclopentyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid

HRID 253123Notes

Reaction equation

HRID 253123 reaction equation
C1([O:6][C:7]([C:9]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[N:10]=2)=[O:8])CCCC1.[OH-].[Na+].Cl>C1COCC1.O>[CH:16]1([N:11]2[C:12](=[O:15])[CH:13]=[CH:14][C:9]([C:7]([OH:8])=[O:6])=[N:10]2)[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66845103Cyclopentyl-1-cyclopentyl-6-oxo-1,6-dihydropyridazine-3-carboxylate

Product 1

HCID 612656941-Cyclopentyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

Cyclopentyl-1-cyclopentyl-6-oxo-1,6-dihydropyridazine-3-carboxylate (20 mg, 0.072 mmol) was dissolved in 2 ml THF/water (1/1) and 2 ml NaOH (5M, aq.) was added. The reaction was stirred at 40° C. for 2 h and 5 ml HCl (5M, aq.) was added. The reaction was concentrated and 10 ml of CH2Cl2/MeOH (1/1) was added and the reaction was sonicated for 10 min and filtered. The filtrate was concentrated and used in the next step without further purification. Yield: 11 mg (0.052 mmol, 73%, film, MS m/z: 209(100%, M+1).

Workup

  1. concentrationThe reaction was concentrated
  2. addition10 ml of CH2Cl2/MeOH (1/1) was added
  3. customthe reaction was sonicated for 10 min
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customused in the next step without further purification

Sources & evidence

ORD record
ord-910e332bbd4b4ffc942f16b44b814d46
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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