Pyridine → HCID 44608226, compound

HRID 1943673Notes

Reaction equation

HRID 1943673 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([OH:7])=O.CN(C)C=O.[O:17]1[CH2:22][CH2:21][NH:20][C:19]2[CH:23]=[N:24][CH:25]=[CH:26][C:18]1=2.N1C=CC=CC=1>S(Cl)(Cl)=O.CN(C)C(=O)C>[Cl:11][C:9]1[CH:8]=[C:4]([C:5]([N:20]2[CH2:21][CH2:22][O:17][C:18]3[CH:26]=[CH:25][N:24]=[CH:23][C:19]2=3)=[O:7])[CH:3]=[C:2]([Cl:1])[N:10]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 948302,6-Dichloroisonicotinic acidHCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazine

Product 1

HCID 44608226HCID 44608226, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 24386Thionyl ChlorideSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

In a 25 ml flask, 2,6-dichloro-isonicotinic acid (100 mg, 0.52 mmol) was dissolved in thionylchloride (0.76 ml), and a catalytic amount of N,N-dimethyl formamide was added thereto and then stirred for 4 hours under reflux. Thionyl chloride was removed under reduced pressure, and 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (78 mg, 0.57 mmol) and pyridine (0.13 ml) were added to the reaction flask and dissolved in N,N-dimethyl acetamide (2.6 ml) and then stirred at room temperature for 18 hours. The reaction mixture was extracted with dichloromethane, and the combined organic layer was dried over anhydrous magnesium sulfate (MgSO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of n-hexane:ethyl acetate=2:1. The fractions containing the product were collected and evaporated to obtain the target compound 31 as yellow solid (116 mg, 72%).

Workup

  1. temperatureunder reflux
  2. additionwere added to the reaction flask
  3. stirringstirred at room temperature for 18 hours
  4. extractionThe reaction mixture was extracted with dichloromethane
  5. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate (MgSO4)
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica eluting with a solvent of n-hexane
  8. additionThe fractions containing the product
  9. customwere collected
  10. customevaporated

Sources & evidence

ORD record
ord-74f6fee72a4f4971b413c04636f114b6
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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