Pyridine → HCID 69587897, compound

HRID 1247012Notes

Reaction equation

HRID 1247012 reaction equation
[OH:1][C@H:2]([CH3:16])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:15])[C:11]=2[N:13]=O)[CH:6]=[N:5]1.N1C=CC=CC=1.[CH3:23][O:24][CH2:25][C:26](Cl)=O>O1CCCC1.CN(C)C1C=CN=CC=1.[Pd]>[CH3:23][O:24][CH2:25][C:26]1[O:15][C:10]2[CH:9]=[CH:8][C:7]3[CH:6]=[N:5][N:4]([CH2:3][C@H:2]([OH:1])[CH3:16])[C:12]=3[C:11]=2[N:13]=1

Participants

7

Reactant 3

HCID 1049Pyridine2×HCID 96623Methoxyacetyl chlorideHCID 136335133HCID 136335133, compound

Product 1

HCID 69587897HCID 69587897, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Step A (1.05 g, 4.75 mol) in tetrahydrofuran (50 mL) containing 10% palladium-on-carbon (0.1 g) was stirred under an atmosphere of hydrogen at room temperature for 18 hours. The reaction mixture was filtered, pyridine (1.0 mL, 12.3 mol) and methoxy acetyl chloride (0.43 mL, 4.75 mol) were added, and this mixture was stirred at room temperature. More pyridine (5.0 mL) was added and the reaction mixture was stirred at room temperature for 20 minutes followed by the addition of 4-dimethylaminopyridine (0.1 g); this mixture was heated at 60° C. for 3 hours followed by removal of solvents by heating at 220° C. for 30 minutes. The resulting dark liquid was purified by chromatography (silica gel, hexane/ethyl acetate gradient) to give a yellow oil (200 mg, 16%): LC/MS m/z 262.

Workup

  1. filtrationThe reaction mixture was filtered
  2. stirringthis mixture was stirred at room temperature
  3. stirringthe reaction mixture was stirred at room temperature for 20 minutes
  4. temperaturethis mixture was heated at 60° C. for 3 hours
  5. customfollowed by removal of solvents
  6. temperatureby heating at 220° C. for 30 minutes
  7. customThe resulting dark liquid was purified by chromatography (silica gel, hexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-4f03f2d44df7402d9b6109f56eaa9e7e
Source dataset
uspto-grants-2006_10
Patent number
US07129257B1

Reaction notes

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