Sodium Acetate → HCID 15981234, compound

HRID 271168Notes

Reaction equation

HRID 271168 reaction equation
C([O-])(=[O:3])C.[Na+].[Br:6][C:7]1[CH:8]=[C:9]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH:10]=[C:11]([Br: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>[Br:6][C:7]1[CH:8]=[C:9]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH:10]=[C:11]([Br: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 59834486HCID 59834486, compound

Product 1

HCID 15981234HCID 15981234, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of glacial acetic acid (16.7 mL), sodium acetate (480 mg, 5.85 mmol) and [3,5-dibromo-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-proprionic acid (22) (800 mg, 1.67 mmol) was heated to 120° C. for 24 h. The reaction mixture was cooled to room temperature and concentrated. The resulting residue was diluted with water (200 mL) and was made basic to pH=9 by the addition of a 1N aqueous sodium hydroxide solution. This solution was extracted with ethyl acetate (1×100 mL) and the ethyl acetate was discarded. The water layer was acidified to pH=3 by the addition of a 1N aqueous hydrochloric acid solution. The water layer was extracted with ethyl acetate (3×100 mL). The organic layers were combined, dried with sodium sulfate, filtered and concentrated under vacuum. The resulting solid was slurried in ethyl acetate (20 mL). Heptane (20 mL) was added to this mixture. The solvents were then concentrated under vacuum to a volume of approximately 20 mL. The solids were filtered and washed with a 1:1 ethyl acetate:heptane solution (2×10 mL). The solid was dried under high vacuum to afford [3,5-dibromo-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-proprionic acid (23) (553 mg, 72%) as an off-white solid; LRMS for C16H16Br2N2O4 (M+H) m/z=461. Molecular Weight=460.1249; Exact Mass=457.9477

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additionThe resulting residue was diluted with water (200 mL)
  4. additionwas made basic to pH=9 by the addition of a 1N aqueous sodium hydroxide solution
  5. extractionThis solution was extracted with ethyl acetate (1×100 mL)
  6. additionThe water layer was acidified to pH=3 by the addition of a 1N aqueous hydrochloric acid solution
  7. extractionThe water layer was extracted with ethyl acetate (3×100 mL)
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. additionHeptane (20 mL) was added to this mixture
  12. concentrationThe solvents were then concentrated under vacuum to a volume of approximately 20 mL
  13. filtrationThe solids were filtered
  14. washwashed with a 1:1 ethyl acetate
  15. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-2f6038682ef54eaeadd37bda9e85ad72
Source dataset
uspto-grants-2008_11
Patent number
US07452882B2

Reaction notes

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