Water → HCID 68291660, compound

HRID 1408899Notes

Reaction equation

HRID 1408899 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([CH:13]=[CH:14][CH:15]=2)[N:5]=[CH:6][C:7]=1[C:8]([O:10]CC)=[O:9].O>C1COCC1>[Cl:1][C:2]1[C:3]2[N:4]([CH:13]=[CH:14][CH:15]=2)[N:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 962WaterHCID 67965620Pyrrolo[1,2-b]pyridazine-3-carboxylic acid, 4-chloro-, ethyl ester

Product 1

HCID 68291660HCID 68291660, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

Dissolved ethyl 4-chloropyrrolo[1,2-b]pyridazine-3-carboxylate (Preparation 2 from Step 5B, 2 g, 8.90 mmol) in THF (12 mL) and added water (2 mL) followed by monohydrated lithium hydroxide (0.747 g, 17.81 mmol) and the resulting yellow mixture was sonicated to give a fine dispersion followed by heating to 55° C. and stirring vigorously for one hour. After removing the organics under vacuum, the resulting residue was dissolved in ˜50 mL of water and 6 N aqueous HCl added until acidic giving a yellow slurry of the product. The product was extracted with ethyl acetate, washed with brine, dried over Na2SO4, decanted and conc. in vacuo to afford 1.8 g (˜quant.) of a yellow solid as the title compound. LCMS (condition B): m/z=197.1, 199.0. HPLC (condition B): Retention time=2.59 min.

Workup

  1. customthe resulting yellow mixture was sonicated
  2. customto give a fine dispersion
  3. customAfter removing the organics under vacuum
  4. dissolutionthe resulting residue was dissolved in ˜50 mL of water
  5. addition6 N aqueous HCl added
  6. customuntil acidic giving a yellow slurry of the product
  7. extractionThe product was extracted with ethyl acetate
  8. washwashed with brine
  9. dry with materialdried over Na2SO4
  10. customdecanted and conc. in vacuo

Sources & evidence

ORD record
ord-6f4a476423954ecf9b910a7a2e5aaa74
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

Loading…