Hexane → HCID 86607566, compound

HRID 2219470Notes

Reaction equation

HRID 2219470 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.C[Al](C)C.CCCCCC.C[O:20][C:21]([C:23]1[C:28]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:27][CH:26]=[C:25]([CH3:37])[N:24]=1)=O>O1CCOCC1>[C:33]([O:32][C:30](=[O:31])[NH:29][C:28]1[C:23]([C:21](=[O:20])[NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)=[N:24][C:25]([CH3:37])=[CH:26][CH:27]=1)([CH3:36])([CH3:34])[CH3:35]

Participants

6

Reactant 4

HCID 8058HexaneHCID 844322-Chloropyridin-4-amineHCID 16682925TrimethylaluminumHCID 59363634HCID 59363634, compound

Product 1

HCID 86607566HCID 86607566, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-chloro-4-aminopyridine (0.97 g, 7.5 mmol, 4.0 equiv.) in dry dioxane (20.0 ml) were added 3.75 ml of a 2M solution of trimethyl aluminium in hexane (7.5 mmol, 4.0 equiv.) and the mixture was stirred for 1 h at r.t.. Then 3-tert-Butoxycarbonylamino-6-methyl-pyridine-2-carboxylic acid methyl ester (0.50 g, 1.88 mmol) were added and the reaction was refluxed for 2 h. After allowing the reaction to cool to r.t., the reaction was quenched with water (0.5 ml), stirred for 5 min, dried by addition of magnesium sulfate and filtered over Dicalite which was further washed with methylene chloride. The filtrate was concentrated in vaccuo. The residue was purified by flash chromatography (heptane/ethyl acetate 2:1) to yield the title compound as a white solid (total 0.50 g, 73%), MS (ISP): m/e=363.1, 365.0 (M+H+).

Workup

  1. temperaturethe reaction was refluxed for 2 h
  2. customthe reaction
  3. temperatureto cool to r.t.
  4. customthe reaction was quenched with water (0.5 ml)
  5. stirringstirred for 5 min
  6. dry with materialdried by addition of magnesium sulfate
  7. filtrationfiltered over Dicalite which
  8. washwas further washed with methylene chloride
  9. concentrationThe filtrate was concentrated in vaccuo
  10. customThe residue was purified by flash chromatography (heptane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-2f1ac1914469408d8c75bed8d7b6c828
Source dataset
uspto-grants-2008_08
Patent number
US07414060B2

Reaction notes

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