Water → HCID 178467653, compound

HRID 1924035Notes

Reaction equation

HRID 1924035 reaction equation
[Si](OCC[N:11]1[C:23]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:16]([O-])=[CH:15][C:14]=2[N:13]=[C:12]1[CH2:25][O:26][CH2:27][CH3:28])(C(C)(C)C)(C)C.[NH4+:29].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>C(Cl)Cl>[CH2:27]([O:26][CH2:25][C:12]1[NH:11][C:23]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[C:15]([NH2:29])[C:14]=2[N:13]=1)[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 67521302HCID 67521302, compound

Product 1

HCID 178467653HCID 178467653, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridine 5-oxide (2.40 g, 5.97 mmol) was dissolved in 60 mL of CH2Cl2 and treated with 6 mL of concentrated aqueous NH4OH solution. The mixture was stirred rapidly and then p-toluenesulfonyl chloride (1.19 g, 6.27 mmol) was carefully added. Rapid stirring was continued for 1.5 hours. The reaction mixture was then treated with 50 mL of CH2Cl2 and 25 mL of H2O. The layers were separated and the organic portion was washed successively with 2% Na2CO3 solution (2×25 mL), H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 10-15% CMA/CHCl3) gave 1-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (1.93 g) as a light-brown foam.

Workup

  1. stirringRapid stirring
  2. customThe layers were separated
  3. washthe organic portion was washed successively with 2% Na2CO3 solution (2×25 mL), H2O and brine
  4. dry with materialThe organic portion was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ce6b571f798b437fa86d8992e4be8d1a
Source dataset
uspto-grants-2012_05
Patent number
US08178539B2

Reaction notes

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