Trifluoroacetic acid → 3-(2-(1-(4-Amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-yloxy)ethylamino)propan-1-ol

HRID 63698Notes

Reaction equation

HRID 63698 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][C:20]([CH3:49])([O:22][CH2:23][CH2:24][NH:25][CH2:26][CH2:27][CH2:28][O:29]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH3:21])[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:18]=1)[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:17][C:9]1[C:8]2[N:18]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:6]([CH2:19][C:20]([CH3:49])([O:22][CH2:23][CH2:24][NH:25][CH2:26][CH2:27][CH2:28][OH:29])[CH3:21])[C:7]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 1184516062-(Ethoxymethyl)-1-[2-methyl-2-[2-(3-trityloxypropylamino)ethoxy]propyl]-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 1184515673-(2-(1-(4-Amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-yloxy)ethylamino)propan-1-olYield 36.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(Ethoxymethyl)-1-[2-methyl-2-[2-(3-trityloxypropylamino)ethoxy]propyl]-imidazo[4,5-c]quinolin-4-amine (10 mg, 15.2 μmol) was combined with DCM (1 mL) to give a colorless solution. TFA (100 μl, 1.3 mmol) was added and the reaction mixture was stirred at room temperature for 5 hours. The mixture was concentrated in vacuo and the residue was purified by flash chromatography (silica gel-NH2, 0% to 30% methanol in ethyl acetate) to give the title compound (2.3 mg, 36%) as colorless gum; LC-MS (UV peak area, ESI) 95.6%, 416.2661 (MH+).

Workup

  1. customto give a colorless solution
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by flash chromatography (silica gel-NH2, 0% to 30% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-d4b743af6b464955a7c395b758b66e82
Source dataset
uspto-grants-2016_09
Patent number
US09447097B2

Reaction notes

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