Triethylamine → 5-{[6-(4-Fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-2-nitroaniline

HRID 517796

Reaction equation

HRID 517796 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[CH:5]=[C:6]([S:13][C:14]#[N:15])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].ClC1N2[N:22]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH:24]=[CH:25][C:20]2=[N:19][N:18]=1.C(N(CC)CC)C>CN(C)C=O.O>[F:32][C:29]1[CH:28]=[CH:27][C:26]([C:23]2[CH:24]=[CH:25][C:20]3[N:15]([C:14]([S:13][C:6]4[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([CH:5]=4)[NH2:3])=[N:18][N:19]=3)[N:22]=2)=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 446043783-Chloro-6-(4-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazineHCID 866478753-Amino-4-nitrophenyl thiocyanate

Product 1

HCID 675246885-{[6-(4-Fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-2-nitroanilineYield 31.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

342 mg of sodium borohydride are added to a mixture of 1.76 g of commercial 3-amino-4-nitrophenyl thiocyanate in 15 cm3 of N,N-dimethylformamide. The reaction is stirred at ambient temperature for 2 h and then 746 mg of 3-chloro-6-(4-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine and 1.25 cm3 of triethylamine are added. The resulting mixture is then heated to 95° C. and then stirred for 1 h at 20° C. After the addition of demineralized water, the mixture obtained is extracted with 3×100 cm3 of ethyl acetate (a small amount of methanol is added due to solubility problems). The organic phases are combined and then dried over magnesium sulphate and concentrated to dryness, so as to give a brown solid which is chromatographed on a 25 g Merck cartridge of silica 15-40 μm (elution with ethyl acetate). 360 mg of 5-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-2-nitroaniline are thus obtained in the form of a green solid, the characteristics of which are as follows:

Workup

  1. temperatureThe resulting mixture is then heated to 95° C.
  2. stirringstirred for 1 h at 20° C
  3. customthe mixture obtained
  4. extractionis extracted with 3×100 cm3 of ethyl acetate (a small amount of methanol
  5. additionis added due to solubility problems)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated to dryness
  8. customso as to give a brown solid which
  9. customis chromatographed on a 25 g Merck cartridge of silica 15-40 μm (elution with ethyl acetate)

Sources & evidence

ORD record
ord-6b9b899563d34cf58707cbf44dba6271
Source dataset
uspto-grants-2015_08
Patent number
US09115134B2

Linked notes

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