Chloroform → 1-[(1S)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropyl]-2-(chloromethyl)-1H-imidazo[4,5-c]quinoline

HRID 1035491Notes

Reaction equation

HRID 1035491 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([NH:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][C:16]=1[NH2:25])[CH:11]([CH3:13])[CH3:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[Cl:27][CH2:28][C:29](=N)OCC.C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>ClCCCl>[Si:1]([O:8][CH2:9][C@@H:10]([N:14]1[C:15]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:25]=[C:29]1[CH2:28][Cl:27])[CH:11]([CH3:13])[CH3:12])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 12470659Ethyl 2-chloroethanecarboximidate hydrochlorideHCID 67156441N'-[(1S)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropyl]quinoline-3,4-diamine

Product 1

HCID 671569611-[(1S)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropyl]-2-(chloromethyl)-1H-imidazo[4,5-c]quinolineYield 82.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

N4-[(1S)-1-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-2-methylpropyl]quinoline-3,4-diamine (5.05 g, 14.0 mmol) was dissolved in 140 mL of dry 1,2-dichloroethane and the solution was stirred under N2. Ethyl 2-chloroethanimidoate hydrochloride (3.33 g, 21.1 mmol) was then added and the reaction mixture was heated to 70° C. After stirring for 2 days, the reaction mixture was cooled and treated with 70 mL of CHCl3 and 100 mL of saturated sodium bicarbonate (NaHCO3) solution. The layers were separated and the organic portion was washed with H2O and brine. The organic portion was then dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 33%-50% ethyl acetate/hexanes) gave 1-[(1S)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropyl]-2-(chloromethyl)-1H-imidazo[4,5-c]quinoline (4.85 g) as a dull yellow solid.

Workup

  1. stirringAfter stirring for 2 days
  2. temperaturethe reaction mixture was cooled
  3. customThe layers were separated
  4. washthe organic portion was washed with H2O and brine
  5. dry with materialThe organic portion was then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f20ddc8a87824cc784ca851576034e16
Source dataset
uspto-grants-2013_10
Patent number
US08546383B2

Reaction notes

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