Trifluoroacetic acid → HCID 66710870, compound

HRID 2089937Notes

Reaction equation

HRID 2089937 reaction equation
[N:1]1([CH:10]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:11]2[C:16](=[O:17])[CH:15]=[CH:14][N:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[N:12]=2)C2C=CC=CC=2[N:3]=[N:2]1.[N-]=[N+]=[N-].[Na+].FC(F)(F)C(O)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[C:29]1([N:28]2[C:10]([C:11]3[C:16](=[O:17])[CH:15]=[CH:14][N:13]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=4)[N:12]=3)=[N:1][N:2]=[N:3]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 86673246HCID 86673246, compound

Product 1

HCID 66710870HCID 66710870, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[1H-benzotriazol-1-yl(phenylamino)methyl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (0.094 g, 0.20 mmol), sodium azide (0.030 g, 0.46 mmol), and tetrabutylammonium bromide (0.015 g, 0.047 mmol) in methylene chloride (5 mL) and water (5 mL) was treated with trifluoroacetic acid (0.040 mL, 0.52 mmol) and stirred 24 h at room temperature. After that time, the organic layer was separated and the aqueous layer was extracted with methylene chloride (3×25 mL). The combined organic extracts were washed with saturated NaCl aqueous solution (50 mL), dried (MgSO4), and concentrated. The crude product purified by flash column chromatography (silica gel, 80:20 hexanes/ethyl acetate to ethyl acetate) to give an off-white solid that was recrystallized from ethyl acetate/hexanes to give 0.034 g (56%) of 3-(1-phenyl-1H-tetrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one as colorless crystals.

Workup

  1. customAfter that time, the organic layer was separated
  2. extractionthe aqueous layer was extracted with methylene chloride (3×25 mL)
  3. washThe combined organic extracts were washed with saturated NaCl aqueous solution (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product purified by flash column chromatography (silica gel, 80:20 hexanes/ethyl acetate to ethyl acetate)
  7. customto give an off-white solid
  8. customthat was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b5527230649b4a8799d90a31b0d00e13
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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