Ammonia → HCID 10571424, compound

HRID 363305Notes

Reaction equation

HRID 363305 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH:7]=[CH:8][CH:9]=1)=[N+]=[N-].[F:19][C:20]([F:26])([F:25])[S:21]([OH:24])(=[O:23])=[O:22].FC(F)(F)C(O)=O.N>>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[C:7]([O:24][S:21]([C:20]([F:26])([F:25])[F:19])(=[O:23])=[O:22])=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 10848408HCID 10848408, compound

Product 1

HCID 10571424HCID 10571424, compoundYield 70%

Conditions

Temperature
20 °C

Procedure

2-(3-Azidophenyl)benzothiazole (1 g) was added in small portions (5×0.2 g) to a mixture of trifluoromethanesulphonic acid (4 ml), trifluoroacetic acid (5 ml) and triflucromethylacetic anhydride (1 ml) at 0° C. After evolution of nitrogen ceased, the mixture was stirred at 20° C. for 18 hours, basified with aqueous ammonia and the products extracted into ethyl acetate. The organic layer was washed with water, dried (MgSO4) and evaporated to give a gum which was separated on silica with hexane-ethyl acetate (6:4) as eluent. The product obtained was the title compound (70% yield). (Found: M+ 374. C14H9F3N2O3S2 requires MW 374). An in vitro assay of this compound against MCF-7 (wild type) cells gave an IC50 value of 50 nM which again indicates a useful level of activity.

Workup

  1. extractionthe products extracted into ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a gum which
  6. customwas separated on silica with hexane-ethyl acetate (6:4) as eluent
  7. customThe product obtained

Sources & evidence

ORD record
ord-03ace695328b45f7a0b0b942b2fbbd9a
Source dataset
uspto-grants-1999_02
Patent number
US05874431

Reaction notes

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