1-Benzylpiperazine → HCID 10429053, compound

HRID 750750Notes

Reaction equation

HRID 750750 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2OS(C(F)(F)F)(=O)=O)[S:4][C:3]=1[C:19](=[O:21])[NH2:20].[CH2:22]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCOCC1>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[N:32]2[CH2:33][CH2:34][N:29]([CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:30][CH2:31]2)[S:4][C:3]=1[C:19]([NH2:20])=[O:21]

Participants

4

Reactant 2

HCID 759941-BenzylpiperazineHCID 23401030HCID 23401030, compound

Product 1

HCID 10429053HCID 10429053, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 20 mg trifluoromethanesulfonic acid 3-amino-2-carbamoyl-thieno[2,3-b]pyridin-4-yl ester and 50 microL of N-benzylpiperazine in 1 mL of dry dioxane was purged with N2 and capped and left at room temperature overnight. The reaction was diluted with EtOAc, washed four times with water, dried and concentrated to dryness in vacuo. The product was purified on a 2 mm silica gel prep plate, developing and eluting the band with MeOH—CH2Cl2 mixtures and then concentrating to dryness. The product was re-dissolved in 5-10% MeOH—CH2Cl2, filtered to remove silica gel, concentrated, and dried in vacuo at 60° C. overnight to provide 7.9 mg of the title compound as a beige solid.

Workup

  1. customwas purged with N2
  2. customcapped
  3. additionThe reaction was diluted with EtOAc
  4. washwashed four times with water
  5. customdried
  6. concentrationconcentrated to dryness in vacuo
  7. customThe product was purified on a 2 mm silica gel prep plate
  8. washeluting the band with MeOH—CH2Cl2 mixtures
  9. concentrationconcentrating to dryness
  10. dissolutionThe product was re-dissolved in 5-10% MeOH—CH2Cl2
  11. filtrationfiltered
  12. customto remove silica gel
  13. concentrationconcentrated
  14. customdried in vacuo at 60° C. overnight

Sources & evidence

ORD record
ord-e61b85179219443f93323b6ab8e6a46a
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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