Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 69308198, compound

HRID 2250648Notes

Reaction equation

HRID 2250648 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[N:10]([C:33]([CH2:36][CH3:37])=[CH:34][CH:35]=3)[N:11]=[C:12]([CH2:22][O:23][CH2:24][CH2:25][O:26]C3CCCCO3)[C:13]=2[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:5]=[N:6][CH:7]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[N:10]([C:33]([CH2:36][CH3:37])=[CH:34][CH:35]=3)[N:11]=[C:12]([CH2:22][O:23][CH2:24][CH2:25][OH:26])[C:13]=2[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 68801503HCID 68801503, compound

Product 1

HCID 69308198HCID 69308198, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 4-(4-(5-bromo-3-pyridinyl)-7-ethyl-2-{[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]methyl}pyrrolo[1,2-b]pyridazin-3-yl)butanoate (89 mg) and pyridinium p-toluenesulfonate (0.8 mg) in MeOH (5 mL) was heated under reflux for 2 hours. After evaporation of solvent, the residue was purified by silica gel column chromatography eluting with a mixture of hexane and AcOEt (10:1-1:1) to give ethyl 4-{4-(5-bromo-3-pyridinyl)-7-ethyl-2-[(2-hydroxyethoxy)methyl]pyrrolo[1,2-b]pyridazin-3-yl}butanoate as yellow oil (69 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customAfter evaporation of solvent
  4. customthe residue was purified by silica gel column chromatography
  5. washeluting with a mixture of hexane and AcOEt (10:1-1:1)

Sources & evidence

ORD record
ord-611eb10c3ce74db6babde75e8b0b9c28
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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