Sodium Acetate → [3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acid

HRID 2199114Notes

Reaction equation

HRID 2199114 reaction equation
C([O-])(=[O:3])C.[Na+].[Cl:6][C:7]1[CH:8]=[C:9]([CH2:25][C:26]([OH:28])=[O:27])[CH:10]=[C:11]([Cl:24])[C:12]=1[O:13][C:14]1[N:15]=[N:16][C:17](Cl)=[C:18]([CH:20]([CH3:22])[CH3:21])[CH:19]=1>C(O)(=O)C>[Cl:6][C:7]1[CH:8]=[C:9]([CH2:25][C:26]([OH:28])=[O:27])[CH:10]=[C:11]([Cl:24])[C:12]=1[O:13][C:14]1[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[C:17](=[O:3])[NH:16][N:15]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 59834443[3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid

Product 1

HCID 15981207[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acidYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of glacial acetic acid (200 mL), sodium acetate (6.1 g, 74.4 mmol) and [3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid (18) (8.3 g, 21.96 mmol) was heated to 125° C. for 24 h. The reaction mixture was cooled to room temperature and concentrated. The resulting residue was diluted with methylene chloride (200 mL) and was washed with water (150 mL). The organic layer was separated. Hexanes (3×200 mL) were added to the residue in portions and then subsequently concentrated under vacuum. The resulting semi-solid was diluted with a minimum amount of ether, scratched, and slurried. The resulting white solid was filtered, washed with cold ether and dried under high vacuum overnight to afford [3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acid (19) (5.1 g, 65%) as a white solid; LRMS for C15H14Cl2N2O4 (M+) m/z=357. Molecular Weight=357.1958; Exact Mass=356.0331

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additionThe resulting residue was diluted with methylene chloride (200 mL)
  4. washwas washed with water (150 mL)
  5. customThe organic layer was separated
  6. additionHexanes (3×200 mL) were added to the residue in portions
  7. concentrationsubsequently concentrated under vacuum
  8. additionThe resulting semi-solid was diluted with a minimum amount of ether
  9. filtrationThe resulting white solid was filtered
  10. washwashed with cold ether
  11. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-80bff88c65254ce1b1b9e2da6630f0cc
Source dataset
uspto-grants-2016_06
Patent number
USRE046024E1

Reaction notes

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