Sodium borohydride → HCID 21075790, compound

HRID 1373914Notes

Reaction equation

HRID 1373914 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([N:18]=[CH:19][C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:18][CH2:19][C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69177440HCID 69177440, compound

Product 1

HCID 21075790HCID 21075790, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)(furan-2-ylmethylene)amine (1.86 g, 5.81 mmol) in 20 mL of methanol was treated with NaBH4 (0.659 g, 17.4 mmol) and stirred under an atmosphere of nitrogen. After 18 h the reaction was quenched by addition of 20 mL of water. The reaction mixture was concentrated under reduced pressure and dissolved in CHCl3. The organic portion was washed with 2% Na2CO3 solution, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)(furan-2-ylmethyl)amine (1.70 g) as a thick orange syrup.

Workup

  1. customAfter 18 h the reaction was quenched by addition of 20 mL of water
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutiondissolved in CHCl3
  4. washThe organic portion was washed with 2% Na2CO3 solution, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e00c4c06eead4bacba633652b4748d8b
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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