Triethylamine → HCID 57455398, compound

HRID 2366693Notes

Reaction equation

HRID 2366693 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:9][CH:8]=[CH:7][CH:6]=2.[C:21](Cl)(=O)[CH2:22][CH2:23][CH3:24].C(N(CC)CC)C.Cl.N1C=CC=CC=1>ClCCl.C(O)C>[CH2:22]([C:21]1[N:12]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]2[C:10]3[N:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 10176127Pyridinium chlorideHCID 57455388HCID 57455388, compound

Product 1

HCID 57455398HCID 57455398, compoundYield 102%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 4-(3-amino[1,5]naphthyridin-4-ylamino)butanoate (2.0 g, 7.3 mmol) in dichloromethane (35 mL) was cooled to 0° C. Butyryl chloride (0.68 mL, 8.0 mmol) was added dropwise over a period of ten minutes, and the reaction was allowed to warm to ambient temperature, stirred for 90 minutes, and concentrated under reduced pressure. Triethylamine (3.0 mL, 22 mmol) and ethanol (35 mL) were added, and the resulting solution was heated at reflux for two days. Pyridine hydrochloride (0.1 equivalents) was added, and the reaction was heated at reflux overnight. The solvent was removed under reduced pressure, and the residue was partitioned between dichloromethane (70 mL) and saturated aqueous sodium bicarbonate (50 mL). The aqueous layer was separated and extracted with dichloromethane (2×25 mL), and the combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 2.43 g of ethyl 4-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]butanoate as a brown oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. temperaturethe resulting solution was heated
  3. temperatureat reflux for two days
  4. temperaturethe reaction was heated
  5. temperatureat reflux overnight
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was partitioned between dichloromethane (70 mL) and saturated aqueous sodium bicarbonate (50 mL)
  8. customThe aqueous layer was separated
  9. extractionextracted with dichloromethane (2×25 mL)
  10. dry with materialthe combined organic fractions were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c90a56103d9145d6af7e8e077fc880f7
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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