HCID 118451572, compound → HCID 118451556, compound

HRID 522843Notes

Reaction equation

HRID 522843 reaction equation
C(OC([NH:11][C:12]1[C:21]2[N:22]=[C:23]([CH2:48][O:49][CH2:50][CH3:51])[N:24]([CH2:25][C:26]([O:29][C:30](=[O:47])[CH2:31][N:32](CC3C=CC=CC=3)CC3C=CC=CC=3)([CH3:28])[CH3:27])[C:20]=2[C:19]2[CH:18]=[CH:17][C:16]([CH2:52][CH2:53][C:54]([O:56][CH2:57][CH3:58])=[O:55])=[CH:15][C:14]=2[N:13]=1)=O)C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[NH2:11][C:12]1[C:21]2[N:22]=[C:23]([CH2:48][O:49][CH2:50][CH3:51])[N:24]([CH2:25][C:26]([O:29][C:30](=[O:47])[CH2:31][NH2:32])([CH3:28])[CH3:27])[C:20]=2[C:19]2[CH:18]=[CH:17][C:16]([CH2:52][CH2:53][C:54]([O:56][CH2:57][CH3:58])=[O:55])=[CH:15][C:14]=2[N:13]=1

Participants

4

Reactant 1

HCID 118451572HCID 118451572, compound

Product 1

HCID 118451556HCID 118451556, compoundYield 5.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 3-(4-(benzyloxycarbonylamino)-1-(2-(2-(dibenzylamino)acetoxy)-2-methylpropyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-yl)propanoate (182 mg, 232 μmol) was combined with ethyl acetate (20 mL) to give a light yellow solution. Palladium on carbon 10% (600 mg, 232 μmol) was added and the mixture was stirred for 20 h at room temperature under H2. Afterwards the mixture was filtered through Celite® and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 20 g, 0% to 30% methanol in THF) to 27 mg of an impure sample that was further purified by preparative HPLC to give the title compound (6 mg, 5%) as light yellow oil; LC-MS (UV peak area, ESI) 79%, 516.5 (MHCOO−).

Workup

  1. customto give a light yellow solution
  2. filtrationAfterwards the mixture was filtered through Celite®
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by flash chromatography (silica gel, 20 g, 0% to 30% methanol in THF) to 27 mg of an impure sample that
  5. customwas further purified by preparative HPLC

Sources & evidence

ORD record
ord-42a172ee511c415bbdda6a524a65061a
Source dataset
uspto-grants-2016_05
Patent number
US09334268B2

Reaction notes

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