4-Toluenesulfonyl chloride → HCID 86587469, compound

HRID 897375Notes

Reaction equation

HRID 897375 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[N:18]=[C:17]([C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[S:30]([N:33]([CH3:35])[CH3:34])(=[O:32])=[O:31])=[O:20])[C:16]([OH:36])=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2.[C:37]1([CH3:47])[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1>C(Cl)(Cl)Cl>[CH3:47][C:37]1[CH:42]=[CH:41][C:40]([S:43]([O:36][C:16]2[C:17]([C:19]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[S:30]([N:33]([CH3:34])[CH3:35])(=[O:32])=[O:31])=[O:20])=[N:18][C:9]([Br:8])=[C:10]3[C:15]=2[N:14]=[CH:13][CH:12]=[CH:11]3)(=[O:45])=[O:44])=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 22346388HCID 22346388, compound

Product 1

HCID 86587469HCID 86587469, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (0.65 mL, 4.66 mmol) was added slowly to a suspension of 5-bromo-N-{2-[(dimethylamino)sulfonyl]-4-fluorobenzyl}-8-hydroxy-1,6-naphthyridine-7-carboxamide (1.50 g, 3.10 mmol) in chloroform (15 mL) to give a yellow cloudy solution. p-Toluenesulfonyl chloride (0.71 g, 3.73 mmol) was then added slowly and the mixture was aged at 40° C. for five hours. The mixture was quenched with 10% KHSO4 solution and the layers were separated. The aqueous layer was extracted twice more with CHCl3. The combined organic extracts were washed once with brine, dried over Na2SO4, filtered, and concentrated in vacuo to a crude yellow oil. The oil was dissolved in a minimal amount of CHCl3 and purified on an Isco column (110 g silica) running a 0 to 2.5% MeOH/CHCl3 gradient over 30 minutes. The collected fractions were concentrated in vacuo to afford the desired material as a white solid foam.

Workup

  1. customto give a yellow cloudy solution
  2. customThe mixture was quenched with 10% KHSO4 solution
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted twice more with CHCl3
  5. washThe combined organic extracts were washed once with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to a crude yellow oil
  9. dissolutionThe oil was dissolved in a minimal amount of CHCl3
  10. custompurified on an Isco column (110 g silica)
  11. customover 30 minutes
  12. concentrationThe collected fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-ec04dc576c824e56a6e83180a137f19b
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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