3-bromo-2-chloro-5-(4-ethylpiperazin-1-ylsulfonyl)pyridine → HCID 22052242, compound

HRID 1831480Notes

Reaction equation

HRID 1831480 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH3:18])[CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH:7]=1.[O-:20][CH2:21][CH3:22].[Na+]>C(O)C>[Br:1][C:2]1[C:3]([O:20][CH2:21][CH3:22])=[N:4][CH:5]=[C:6]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH3:18])[CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 10342243-bromo-2-chloro-5-(4-ethylpiperazin-1-ylsulfonyl)pyridineHCID 2723922Sodium ethoxide

Product 1

HCID 22052242HCID 22052242, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the product from stage d) (6.60 g, 17.9 mmol) and sodium ethoxide (6.09 g, 89.55 mmol) in ethanol (100 ml) was heated under reflux for 18 hours, then cooled. The reaction mixture was concentrated under reduced pressure, the residue partitioned between water (100 ml) and ethyl acetate (100 ml), and the layers separated. The aqueous phase was extracted with ethyl acetate (2×100 ml), the combined organic solutions dried (MgSO4) and evaporated under reduced pressure to afford the title compound as a brown solid, 6.41 g; Found: C, 41.27; H, 5.33; N, 11.11. C13H20BrN3O3S requires C, 41.35; H, 5.28; N, 10.99%; δ (CDCl3, 300 MHz): 1.06 (3H, t), 1.48 (3H, t), 2.42 (2H, q), 2.56 (4H, m), 3.09 (4H, m), 4.54 (2H, q), 8.10 (1H, s), 8.46 (1H, s); LRMS: m/z 378, 380 (M+1)+.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperaturecooled
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe residue partitioned between water (100 ml) and ethyl acetate (100 ml)
  6. customthe layers separated
  7. extractionThe aqueous phase was extracted with ethyl acetate (2×100 ml)
  8. dry with materialthe combined organic solutions dried (MgSO4)
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-80852906d875421e815830747266faf0
Source dataset
uspto-grants-2006_06
Patent number
US07067660B2

Reaction notes

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