2,6-Diaminopyridine → HCID 58997339, compound

HRID 1591880Notes

Reaction equation

HRID 1591880 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[C:3]=1[C:4](Cl)=[O:5].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[N:15]=1.O1CCOCC1>C(Cl)Cl>[NH2:13][C:14]1[N:15]=[C:16]([NH:20][C:4](=[O:5])[C:3]2[C:2]([F:1])=[CH:10][C:9]([F:11])=[CH:8][C:7]=2[F:12])[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 88612,6-DiaminopyridineHCID 312751,4-DioxaneHCID 1448952,4,6-Trifluorobenzoyl chloride

Product 1

HCID 58997339HCID 58997339, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Combine 2,4,6-trifluorobenzoyl chloride (3.891 g, 20 mmol), 2,6-diaminopyridine (6.548 g, 60 mmol) and dioxane (25 mL) and stir for 1 hr. at room temperature followed by heating at 40° C. overnight. Dilute the reaction mixture with CH2Cl2 (100 mL), and wash with 0.1N NaOH solution. Extract the aqueous layer three times with CH2Cl2. Combine the organic layers, dry over Na2SO4, filter, and concentrate to a residue. Chromatography on silica gel, eluting with a gradient of 40–50% ethylacetate in hexanes gives the title intermediate (3.95 g, 74%): mass spectrum (ion spray): m/z=267.9 (M+1); 1H NMR (CDCl3, ppm):8.28 (s, br, 1H), 7.66 (d, 1H), 7.52 (t, 1H), 6.78 (m, 2H), 6.31 (d, 1H), 4.36 (s, br, 2H).

Workup

  1. customat room temperature
  2. washwash with 0.1N NaOH solution
  3. extractionExtract the aqueous layer three times with CH2Cl2
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate to a residue
  7. washChromatography on silica gel, eluting with a gradient of 40–50% ethylacetate in hexanes

Sources & evidence

ORD record
ord-5d176bbf50b24ee38dd9de8e2d173d8a
Source dataset
uspto-grants-2007_11
Patent number
US07291632B2

Reaction notes

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