Sodium Bicarbonate → HCID 67156805, compound

HRID 221606

Reaction equation

HRID 221606 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([NH:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:30]=[CH:29][C:28]=1[NH2:37])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[CH:14][CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[Cl:39][CH2:40][C:41](=N)OCC.C([O-])(O)=O.[Na+]>ClCCCl>[Si:1]([O:8][CH2:9][C@@H:10]([N:26]1[C:27]2[C:36]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[N:30]=[CH:29][C:28]=2[N:37]=[C:41]1[CH2:40][Cl:39])[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[CH:16][CH:17]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 12470659Ethyl 2-chloroethanecarboximidate hydrochlorideHCID 86624132HCID 86624132, compound

Product 1

HCID 67156805HCID 67156805, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

N4-[(1S)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-(4-{[tert-butyl(dimethyl)silyl]oxy}benzyl)ethyl]quinoline-3,4-diamine (23.46 g, 43.6 mmol) was dissolved in 400 mL of dry 1,2-dichloroethane and the yellow solution was stirred under N2. Ethyl 2-chloroethanimidoate hydrochloride (13.8 g, 87.2 mmol) was then added and the reaction mixture was heated to 70° C. overnight. The reaction mixture was then cooled and treated with 300 mL of saturated NaHCO3 solution. The layers were separated and the organic portion was washed sequentially with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. Chromatography (SiO2, 10-60% ethyl acetate/hexanes) gave 1-[(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(4-{[tert-butyl(dimethyl)silyl]oxy}benzyl)ethyl]-2-(chloromethyl)-1H-imidazo[4,5-c]quinoline (21.11 g) as a brown foam.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customThe layers were separated
  3. washthe organic portion was washed sequentially with saturated NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-93dc2d059fbb47cdba5ac263c67a0241
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Linked notes

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