Chloroform → HCID 86594226, compound

HRID 1373931Notes

Reaction equation

HRID 1373931 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([N:18]=[CH:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[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+].C(Cl)(Cl)Cl>CO>[NH4+:6].[OH-:3].[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[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

6

Reactant 3

HCID 6212Chloroform2×HCID 4311764Sodium borohydrideHCID 86594225HCID 86594225, compound

Product 2

HCID 14923Ammonium HydroxideHCID 86594226HCID 86594226, compoundYield 162.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of tert-butyl {3-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)imino]propyl}carbamate (1.64 g, 4.13 mmol) in 20 mL of methanol was treated with NaBH4 (0.78 g, 20.6 mmol) under an atmosphere of nitrogen. After 1.5 h, the reaction mixture was quenched with saturated NH4Cl solution and concentrated under reduced pressure. The residue was partitioned between saturated NaHCO3 solution and CHCl3 and the phases were separated. The organic portion was washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a light brown solid. Chromatography [SiO2, 95:5 CHCl3:(80:18:2 CHCl3:MeOH:NH4OH)] yielded tert-butyl {3-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)amino]propyl}carbamate (1.34 g) as a tan foam.

Workup

  1. customthe reaction mixture was quenched with saturated NH4Cl solution
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between saturated NaHCO3 solution and CHCl3
  4. customthe phases were separated
  5. washThe organic portion was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto yield a light brown solid

Sources & evidence

ORD record
ord-9e1325a658094907807936018e3f46d4
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

Loading…