Sodium borohydride → N-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylamine

HRID 1373961Notes

Reaction equation

HRID 1373961 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([N:22]=[C:23]([CH3:25])[CH3:24])[C:20]([CH2:26][O:27][CH2:28][CH3:29])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([NH:22][CH:23]([CH3:25])[CH3:24])[C:20]([CH2:26][O:27][CH2:28][CH3:29])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 21075798N-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamine

Product 1

HCID 21075797N-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylamineYield 85.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of N-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamine (7.69 g, 19.8 mmol) in 50 mL of methanol was cooled to 0° C. The solution was treated with sodium borohydride (1.12 g, 29.7 mmol) over 10 min. The reaction was allowed to slowly come to ambient temperature. After 2 h, the reaction was quenched with 15 mL of saturated NH4Cl solution and concentrated under reduced pressure to yield a tan solid residue. The solid was dissolved in 100 mL of CHCl3 and 25 mL of saturated K2CO3 solution then separated. The organic portion was washed with water (25 mL), brine (25 mL), dried over Na2SO4, filtered and concentrated to yield a brown oil. The oil was purified by chromatography (SiO2, 98:2 CHCl3:MeOH) to yield 6.63 g of N-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylamine as a tan foam.

Workup

  1. customto slowly come to ambient temperature
  2. customthe reaction was quenched with 15 mL of saturated NH4Cl solution
  3. concentrationconcentrated under reduced pressure
  4. customto yield a tan solid residue
  5. custom25 mL of saturated K2CO3 solution then separated
  6. washThe organic portion was washed with water (25 mL), brine (25 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield a brown oil
  11. customThe oil was purified by chromatography (SiO2, 98:2 CHCl3:MeOH)

Sources & evidence

ORD record
ord-c5ae325853de4e19bc4e70424eb35903
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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