Pyridine → HCID 11697421, compound

HRID 910864Notes

Reaction equation

HRID 910864 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[NH2:7][C:8]1[CH:28]=[CH:27][C:11]([O:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[NH:20][CH2:21][C:22]([O:24]CC)=[O:23])=[C:10]([Cl:29])[CH:9]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:19][C:17]1[CH:16]=[CH:15][C:14]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[C:13]([O:12][C:11]2[CH:27]=[CH:28][C:8]([NH:7][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:9][C:10]=2[Cl:29])[CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 67391135HCID 67391135, compound

Product 1

HCID 11697421HCID 11697421, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethanesulphonyl chloride (0.1 ml) was added to a mixture of the product from step (iii) (0.11 g) and pyridine (0.5 ml) in DCM (4 ml). After stirring at room temperature for 4 h the mixture was partitioned between diethylether/2 M HCl. The organics separated, dried and evaporated under reduced pressure. The residue was dissolved in methanol (5 ml) then 2M NaOH added and stirred at room temperature for 20 h. The solvent was removed under reduced pressure and the residue partitioned between ethylacetate/1M HCl. The organics were separated, washed with water, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 80% ethylacetate/isohexane, yield 0.025 g.

Workup

  1. customwas partitioned between diethylether/2 M HCl
  2. customThe organics separated, dried
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in methanol (5 ml)
  5. addition2M NaOH added
  6. stirringstirred at room temperature for 20 h
  7. customThe solvent was removed under reduced pressure
  8. customthe residue partitioned between ethylacetate/1M HCl
  9. customThe organics were separated
  10. washwashed with water
  11. customdried
  12. customevaporated under reduced pressure
  13. customThe residue was purified by chromatography on silica eluting with 80% ethylacetate/isohexane, yield 0.025 g

Sources & evidence

ORD record
ord-8b6f19d406f74165a1654660331abe3a
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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