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

HRID 221528Notes

Reaction equation

HRID 221528 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([NH:14][C:15]1C=NC2C(C=1N)=CC=CC=2)[CH:11]([CH3:13])[CH3:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.Cl[CH2:28][C:29](=[NH:33])OCC.[CH:34]([Cl:37])(Cl)Cl.C(=O)(O)[O-].[Na+].Cl[CH2:44][CH2:45]Cl>>[Si:1]([O:8][CH2:9][C@@H:10]([N:14]1[C:45]2[C:44]3[CH:6]=[CH:4][CH:5]=[CH:28][C:29]=3[N:33]=[CH:9][C:10]=2[N:14]=[C:15]1[CH2:34][Cl:37])[CH:11]([CH3:12])[CH3:13])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 12470659Ethyl 2-chloroethanecarboximidate hydrochlorideHCID 67156490N-[(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]quinoline

Conditions

Temperature
70 °C

Procedure

N-[(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-e8e43afc533c4fbbb5657f9fafbddd88
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Reaction notes

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