1,4-Dioxane → HCID 46203865, compound

HRID 1724870Notes

Reaction equation

HRID 1724870 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1.C([O-])(O)=O.[Na+].O1CCOCC1.Br.Br[CH2:23][C:24]([C:26]1[C:31]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:29]=[CH:28][N:27]=1)=O>O>[F:35][C:32]([F:33])([F:34])[C:31]1[C:26]([C:24]2[N:1]=[C:2]3[N:3]=[CH:4][CH:5]=[C:6]([NH2:9])[C:7]3=[N:8][CH:23]=2)=[N:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 22135565Pyridine-2,3,4-triamineHCID 462042022-Bromo-1-[3-(trifluoromethyl)pyridin-2-yl]ethan-1-one--hydrogen bromide (1/1)

Product 1

HCID 46203865HCID 46203865, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dissolve 2,3,4-triaminopyridine (2.5 mmol) in water (20 mL). Add NaHCO3 (0.63 g, 7.5 mmol), dioxane (10 mL), and 2-bromo-1-(3-trifluoromethyl-pyridin-2-yl)-ethanone hydrobromide (0.5 g) and stir at 100° C. for 2 hours. Cool the mixture and extract with EtOAc (4×10 mL). Wash the combined organic extracts with brine and dry over Na2SO4. Purify the residue by preparative HPLC to give the title compound.

Workup

  1. temperatureCool the mixture
  2. extractionextract with EtOAc (4×10 mL)
  3. washWash the combined organic extracts with brine
  4. dry with materialdry over Na2SO4
  5. customPurify the residue by preparative HPLC

Sources & evidence

ORD record
ord-61395ab9d01848f297c221b3f716704d
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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