Hydrochloric Acid → HCID 67520919, compound

HRID 1924036Notes

Reaction equation

HRID 1924036 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[C:23]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[C:15]([NH2:24])[C:14]=2[N:13]=[C:12]1[CH2:25][O:26][CH2:27][CH3:28])(C(C)(C)C)(C)C.Cl>C(O)C>[NH2:24][C:15]1[C:14]2[N:13]=[C:12]([CH2:25][O:26][CH2:27][CH3:28])[N:11]([CH2:10][CH2:9][OH:8])[C:23]=2[C:22]2[N:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67521924HCID 67521924, compound

Product 1

HCID 67520919HCID 67520919, compoundYield 139.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (1.93 g, 4.81 mmol) was dissolved in 20 mL of ethanol and treated with 1.6 mL of 3 M HCl in ethanol and the mixture was heated to reflux. After 2 hours, the reaction mixture was concentrated under reduced pressure and the resulting residue was partitioned between 50 mL of CHCl3 and 25 mL of dilute NH4OH solution. The layers were separated and the aqueous portion was extracted with additional CHCl3 (12×20 mL). The combined organic portions were washed with 10 mL of brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 25% CMA/CHCl3) gave 2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]ethanol (1.93 g) as a light-yellow powder.

Workup

  1. temperaturethe mixture was heated to reflux
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was partitioned between 50 mL of CHCl3 and 25 mL of dilute NH4OH solution
  4. customThe layers were separated
  5. extractionthe aqueous portion was extracted with additional CHCl3 (12×20 mL)
  6. washThe combined organic portions were washed with 10 mL of brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7717c8d680fe4118a20709943cfc8f17
Source dataset
uspto-grants-2012_05
Patent number
US08178539B2

Reaction notes

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