Acetic Acid → 4-{[6-(4-Fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}benzene-1,2-diamine

HRID 517795Notes

Reaction equation

HRID 517795 reaction equation
C(O)(=O)C.[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([S:21][C:22]4[CH:23]=[CH:24][C:25]([N+:29]([O-])=O)=[C:26]([CH:28]=4)[NH2:27])=[N:19][N:20]=3)[N:17]=2)=[CH:8][CH:7]=1.[OH-].[Na+].O>CO.C(OCC)C.[Fe]>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([S:21][C:22]4[CH:28]=[C:26]([NH2:27])[C:25]([NH2:29])=[CH:24][CH:23]=4)=[N:19][N:20]=3)[N:17]=2)=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 675246885-{[6-(4-Fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-2-nitroaniline

Product 1

HCID 675241354-{[6-(4-Fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}benzene-1,2-diamineYield 52.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

0.6 cm3 of acetic acid and 145 mg of iron(0) are added to a mixture of 146 mg of 5-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-2-nitroaniline in 7 cm3 of methanol. The reaction mixture is then stirred at reflux for 5 h 15 and then overnight at 20° C. before the addition of 10 cm3 of a 5N aqueous solution of sodium hydroxide and 10 cm3 of demineralized water. The mixture obtained is extracted with 2×30 cm3 of ethyl acetate. The combined organic phases are washed with 20 cm3 of water and then dried over magnesium sulphate and concentrated to dryness. The beige solid obtained is taken up in diethyl ether, spin-filter-dried, and then dried under vacuum. 71 mg of 4-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}benzene-1,2-diamine are thus obtained, the characteristics of which are as follows:

Workup

  1. temperatureat reflux for 5 h 15
  2. customThe mixture obtained
  3. extractionis extracted with 2×30 cm3 of ethyl acetate
  4. washThe combined organic phases are washed with 20 cm3 of water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness
  7. customThe beige solid obtained
  8. customspin-filter-dried
  9. customdried under vacuum

Sources & evidence

ORD record
ord-e0588d4853f64e2294dba41bde6f2247
Source dataset
uspto-grants-2015_08
Patent number
US09115134B2

Reaction notes

Loading…