Ethyl orthoformate → HCID 69192155, compound

HRID 1187398Notes

Reaction equation

HRID 1187398 reaction equation
[CH:1](OCC)(OCC)OCC.Cl.N1C=CC=CC=1.[C:18]([O:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][N:34]=2)[N:29]=[CH:28][C:27]=1[NH2:36])(=[O:20])[CH3:19]>C1(C)C=CC=CC=1.ClCCl>[C:18]([O:21][CH2:22][CH2:23][CH2:24][N:25]1[C:26]2[C:35]3[N:34]=[CH:33][CH:32]=[CH:31][C:30]=3[N:29]=[CH:28][C:27]=2[N:36]=[CH:1]1)(=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 31214Ethyl orthoformate2×HCID 10176127Pyridinium chlorideHCID 68539256HCID 68539256, compound

Product 1

HCID 69192155HCID 69192155, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Triethyl orthoformate (1.86 mL, 17.0 mmol) and pyridine hydrochloride (0.164 g, 1.42 mrnmol) were added to a stirred suspension of 3-[(3-amino[1,5]naphthyridin-4-yl)amino]propyl acetate (prepared as described in Part C of Examples 127-135, 3.70 g, 14.2 mmol) in toluene (70 mL). The mixture was heated at reflux with a Dean-Stark trap. After 2.5 hours, additional triethyl orthoformate (1 mL) was added and heating was continued for another 2 hours. The mixture was allowed to cool to room temperature and was concentrated under reduced pressure to afford a dark oil that was dissolved in dichloromethane (100 mL). The solution was washed with saturated aqueous sodium bicarbonate (50 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 3.50 g of 3-(1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propyl acetate as an orange oil that was used without further purification in the next step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux with a Dean-Stark trap
  3. temperatureheating
  4. waitwas continued for another 2 hours
  5. concentrationwas concentrated under reduced pressure
  6. customto afford a dark oil that
  7. washThe solution was washed with saturated aqueous sodium bicarbonate (50 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-665b643b3cdb4fbaaa43d69673013a53
Source dataset
uspto-grants-2014_03
Patent number
US08673932B2

Reaction notes

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