Ammonia → 4-{[6-(4-Fluorophenyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}benzene-1,2-diamine

HRID 517797Notes

Reaction equation

HRID 517797 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([S:17][C:18]4[CH:19]=[CH:20][C:21]([N+:25]([O-])=O)=[C:22]([CH:24]=4)[NH2:23])=[N:15][N:16]=3)[N:13]=2)=[CH:4][CH:3]=1.O.N>C(O)(=O)C.[Zn]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11]3[N:12]([C:14]([S:17][C:18]4[CH:24]=[C:22]([NH2:23])[C:21]([NH2:25])=[CH:20][CH:19]=4)=[N:15][N:16]=3)[N:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 675246885-{[6-(4-Fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-2-nitroaniline

Product 1

HCID 675254934-{[6-(4-Fluorophenyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}benzene-1,2-diamineYield 215.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

422 mg of zinc(0) are added to a solution of 240 mg of 5-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-2-nitroaniline in 13 cm3 of acetic acid and the resulting mixture is stirred for 1 h at 20° C. 30 cm3 of water are then added to the reaction mixture, which is changed to an alkaline medium by adding 16 cm3 of an aqueous solution of ammonia at 28%. The mixture obtained is extracted with ethyl acetate. The resulting organic phase is washed successively with a saturated aqueous solution of sodium hydrogen carbonate and with a saturated aqueous solution of sodium chloride and is then dried over magnesium sulphate, filtered and evaporated to dryness. The residue is made into a paste in ether, filtered, and then dried under vacuum at 20° C. 479 mg of 4-{[6-(4-fluorophenyl)-7,8-dihydro[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. customThe mixture obtained
  2. extractionis extracted with ethyl acetate
  3. washThe resulting organic phase is washed successively with a saturated aqueous solution of sodium hydrogen carbonate and with a saturated aqueous solution of sodium chloride
  4. dry with materialis then dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. filtrationfiltered
  8. customdried under vacuum at 20° C

Sources & evidence

ORD record
ord-8afb77dcca344b6a9bea266c52217a33
Source dataset
uspto-grants-2015_08
Patent number
US09115134B2

Reaction notes

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