1,5-Naphthalenedisulfonic acid → HCID 46224497, compound

HRID 1994181Notes

Reaction equation

HRID 1994181 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([N:13]1[CH2:18][CH2:17][C:16]2[S:19][CH:20]=[CH:21][C:15]=2[CH2:14]1)[C:9]([O:11][CH3:12])=[O:10].[C:22]1([S:36]([OH:39])(=[O:38])=[O:37])[C:31]2[CH:30]=[CH:29][CH:28]=[C:27]([S:32]([OH:35])(=[O:34])=[O:33])[C:26]=2[CH:25]=[CH:24][CH:23]=1.O1CCOCC1.CCCCCCC>C(O)C>[OH2:10].[C:22]1([S:36]([OH:39])(=[O:38])=[O:37])[C:31]2[CH:30]=[CH:29][CH:28]=[C:27]([S:32]([OH:35])(=[O:34])=[O:33])[C:26]=2[CH:25]=[CH:24][CH:23]=1.[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([N:13]1[CH2:18][CH2:17][C:16]2[S:19][CH:20]=[CH:21][C:15]=2[CH2:14]1)[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 66661,5-Naphthalenedisulfonic acidHCID 8900HeptaneHCID 312751,4-Dioxane2×HCID 60606Clopidogrel

Product 1

HCID 46224497HCID 46224497, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Methyl(+)-(S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5(4H) acetate of preparation 1 (1.3013 g) was added to a naphthalene-1,5-disulfonic acid solution in ethanol (1.0498 g in 10 mL of ethanol, 7.00 mL). Additional ethanol (3.00 mL) was added and mixture sonicated until complete dissolution was achieved. 1,4-Dioxane (10.0 mL) was added and the solution was filtered through a 0.2 μm nylon filter into a clean vial. The sample was left to evaporate uncovered. A gel formed which was seeded with Form A of Example 1, followed by the addition of ethanol (1 mL). The mixture was slurried at 40° C. until it completely dissolved. 1,4-Dioxane (8 mL) was added, followed by seeds of Form A of Example 1 and the mixture left to evaporate uncovered. White solids and gel formed and heptane (3.0 mL) was added. The slurry was filtered and solids washed with acetone. Some of the solids (0.0923 g) were slurried in acetone (0.80 mL) at 45° C. The slurry completely dissolved so more of the solids were added and the mixture was slurried at 45-46° C. The slurry was then filtered through a 0.2 μm nylon filter into a clean vial, capped, and placed in a water bath at 54° C., which was then slowly cooled to ambient temperature. Solids precipitated and the mixture was refrigerated, then filtered through a 0.2 μm filter, and solids left in the vial were dried under nitrogen to afford the title compound, m.p. 218° C., which was analyzed by FTIR and XRPD.

Workup

  1. custommixture sonicated until complete dissolution
  2. filtrationthe solution was filtered through a 0.2 μm nylon
  3. filtrationfilter into a clean vial
  4. waitThe sample was left
  5. customto evaporate
  6. customA gel formed which
  7. customwas slurried at 40° C. until it
  8. dissolutioncompletely dissolved
  9. waitthe mixture left
  10. customto evaporate
  11. customWhite solids and gel formed
  12. filtrationThe slurry was filtered
  13. washsolids washed with acetone
  14. customwere slurried in acetone (0.80 mL) at 45° C
  15. dissolutionThe slurry completely dissolved so more of the solids
  16. additionwere added
  17. customwas slurried at 45-46° C
  18. filtrationThe slurry was then filtered through a 0.2 μm nylon
  19. filtrationfilter into a clean vial
  20. customcapped
  21. customplaced in a water bath at 54° C.
  22. customSolids precipitated
  23. filtrationfiltered through a 0.2 μm
  24. filtrationfilter
  25. waitsolids left in the
  26. customvial were dried under nitrogen

Sources & evidence

ORD record
ord-3e08889d9c3243dfa6ffae347cda4d74
Source dataset
uspto-grants-2010_01
Patent number
US07652139B2

Reaction notes

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