Triethylamine → HCID 67521562, compound

HRID 1924033Notes

Reaction equation

HRID 1924033 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][N:20]=2)[N:15]=[CH:14][C:13]=1[NH2:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:30]([O:32][CH2:33][C:34](Cl)=O)[CH3:31]>C(Cl)Cl.C(O)C>[Si:1]([O:8][CH2:9][CH2:10][N:11]1[C:12]2[C:21]3[N:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=[C:31]1[CH2:30][O:32][CH2:33][CH3:34])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 84189Ethoxyacetyl chlorideHCID 86643248HCID 86643248, compound

Product 1

HCID 67521562HCID 67521562, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N4-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)[1,5]naphthyridine-3,4-diamine (2.12 g, 6.67 mmol) was dissolved in 35 mL of anhydrous CH2Cl2 and the solution cooled to 0° C. and stirred under N2. Triethylamine (974 μL, 7.00 mmol) and ethoxyacetyl chloride (768 μL g, 7.00 mmol) were then added and the reaction mixture was stirred for 1 hour. The reaction mixture was then concentrated under reduced pressure to give a brown syrup. The brown syrup was dissolved in 50 mL of ethanol and treated with 4 mL of triethylamine. The mixture was heated to reflux for 3 days and then concentrated under reduced pressure. The resulting material was dissolved in 50 mL of CH2Cl2 and washed successively with H2O (2×50 mL) and brine (50 mL). The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 10-20% CMA/CHCl3), gave 2.30 g of 1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridine as a purple solid.

Workup

  1. stirringthe reaction mixture was stirred for 1 hour
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customto give a brown syrup
  4. temperatureThe mixture was heated
  5. temperatureto reflux for 3 days
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe resulting material was dissolved in 50 mL of CH2Cl2
  8. washwashed successively with H2O (2×50 mL) and brine (50 mL)
  9. dry with materialThe organic portion was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12cf836e70ef4bb2b5b422cf04fe8c8a
Source dataset
uspto-grants-2012_05
Patent number
US08178539B2

Reaction notes

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