Ethyl Acetate → 6-(Di-pyridin-2-yl-amino)-hexanoic acid methyl ester

HRID 523890

Reaction equation

HRID 523890 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23].CCOC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[CH3:25][O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][N:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 145472,2'-DipyridylamineHCID 24758Sodium hydrideHCID 4170292Methyl 6-Bromohexanoate

Product 1

HCID 585450216-(Di-pyridin-2-yl-amino)-hexanoic acid methyl esterYield 24%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

NaH (112 mg, 2.92 mmol) was added to di-pyridin-2-yl-amine (500 mg, 2.92 mmol) in DMF (10 mL) at rt. After 10 min, KI (485 mg, 2.92 mmol) and methyl 6-bromohexanoate, I (0.464 mL, 2.92 mmol) were added, and the reaction mixture was stirred at 90° C. for 21 h. Brine (200 mL) and EtOAc (200 mL) were then added, the phases were separated, and the aqueous phase was extracted with EtOAc (100 mL). The organic phases were combined, dried over MgSO4, filtered, and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using CH2Cl2/MeOH (100:0.5 to 100:1) as eluant to furnish II as a colourless oil (206 mg, 24%).

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with EtOAc (100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customsubsequently evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dda988683dcb4ad090714d9dc99b5942
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Linked notes

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