Trifluoroacetic acid → 1-(2-(2-Aminoethoxy)-2-methylpropyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 522825Notes

Reaction equation

HRID 522825 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:38][C:39]([CH3:52])([O:41][CH2:42][CH2:43][NH:44]C(=O)OC(C)(C)C)[CH3:40])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH:17]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:8]=2[N:37]=1)[CH3:2].C(O)(C(F)(F)F)=O.[OH-].[Na+]>ClCCl>[NH2:44][CH2:43][CH2:42][O:41][C:39]([CH3:40])([CH3:52])[CH2:38][N:6]1[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:37]=[C:5]1[CH2:4][O:3][CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 118460900tert-Butyl 2-(1-(2-(ethoxymethyl)-4-(tritylamino)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-yloxy)ethylcarbamate

Product 1

HCID 1184515851-(2-(2-Aminoethoxy)-2-methylpropyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amineYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-(1-(2-(ethoxymethyl)-4-(tritylamino)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-yloxy)ethylcarbamate (1.45 g, 2.07 mmol) was combined with dichloromethane (DCM, 12 mL) to give a colorless solution. TFA (6.0 mL, 77.9 mmol) was added and the mixture was stirred for 3 hours at room temperature. The reaction mixture was cooled to 0° C., 2N sodium hydroxide solution (40 mL) was added, and the basic solution was extracted with dichloromethane. Organic layers were combined, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 0 to 10% methanol in DCM) to give the title compound (0.62 g, 83%) as white solid; LC-MS (UV peak area, ESI) 97.5%, 358.2238 (MH+).

Workup

  1. customto give a colorless solution
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. extractionthe basic solution was extracted with dichloromethane
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (silica gel, 0 to 10% methanol in DCM)

Sources & evidence

ORD record
ord-ae7915ca47544db3913f22015147cb62
Source dataset
uspto-grants-2016_05
Patent number
US09334268B2

Reaction notes

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