Sodium Hydroxide → 4-(1-(Tert-butoxycarbonyl)piperidin-4-yloxy)-1-(3,4-dichlorophenyl)-6-oxo-1,6-dihydropyridazine-3-carboxylic acid

HRID 386548Notes

Reaction equation

HRID 386548 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:16]([C:30]([O:32]C)=[O:31])=[N:17][N:18]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=3)[C:19](=[O:21])[CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[C:16]([C:30]([OH:32])=[O:31])=[N:17][N:18]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=3)[C:19](=[O:21])[CH:20]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44621627Methyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(3,4-dichlorophenyl)-6-oxo-1,6-dihydropyridazine-3-carboxylate

Product 1

HCID 670726944-(1-(Tert-butoxycarbonyl)piperidin-4-yloxy)-1-(3,4-dichlorophenyl)-6-oxo-1,6-dihydropyridazine-3-carboxylic acidYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(3,4-dichlorophenyl)-6-oxo-1,6-dihydropyridazine-3-carboxylate (example 14) (59.8 mg, 0.12 mmol) in THF (2 mL) at room temperature under argon was added 2M NaOH (0.18 mL, 0.36 mmol). The reaction mixture was stirred at room temperature overnight. Most of the product was precipitated out. Solvents were removed in vacuo. 10 mL of water and 1 mL of 1 M HCl were added. The product was collected by filtration and further washed with water (3 mL×2). After drying overnight, 56.7 mg (96%) of 4-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(3,4-dichlorophenyl)-6-oxo-1,6-dihydropyridazine-3-carboxylic acid was obtained as a white solid. MS (ESI) 428 (M+H-tBu).

Workup

  1. customMost of the product was precipitated out
  2. customSolvents were removed in vacuo
  3. addition10 mL of water and 1 mL of 1 M HCl were added
  4. filtrationThe product was collected by filtration
  5. washfurther washed with water (3 mL×2)
  6. customAfter drying overnight

Sources & evidence

ORD record
ord-40f065b757e04f4bb81ae790b82bc777
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

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