1-acetyl-4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidin-4-ol → HCID 57515415, compound

HRID 1363567Notes

Reaction equation

HRID 1363567 reaction equation
C(N1CCC(CN2C3C4C=CC=CC=4N=CC=3N=[C:13]2[CH2:25][O:26][CH2:27]C)(O)CC1)(=O)C.[C:29]([N:32]1[CH2:37][CH2:36][C:35]([CH2:45][N:46]2[C:58]3[C:57]4[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=4[N:51]=[CH:50][C:49]=3[N:48]=[C:47]2[CH2:59]OCC)([O:38][CH2:39][CH2:40][S:41]([CH3:44])(=[O:43])=[O:42])[CH2:34][CH2:33]1)(=[O:31])[CH3:30]>>[C:29]([N:32]1[CH2:33][CH2:34][C:35]([CH2:45][N:46]2[C:58]3[C:57]4[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=4[N:51]=[CH:50][C:49]=3[N:48]=[C:47]2[CH2:59][CH2:27][O:26][CH2:25][CH3:13])([O:38][CH2:39][CH2:40][S:41]([CH3:44])(=[O:42])=[O:43])[CH2:36][CH2:37]1)(=[O:31])[CH3:30]

Participants

3

Reactant 2

HCID 575154131-acetyl-4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidin-4-olHCID 57515414HCID 57515414, compound

Product 1

HCID 57515415HCID 57515415, compoundYield 13%

Procedure

1-Acetyl-4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidin-4-ol (1.80 g, 4.68 mmol) was converted into 1-({1-acetyl-4-[2-(methylsulfonyl)ethoxy]piperidin-4-yl}methyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinoline according to the method described in Part A of Example 13. Purification by flash chromatography (silica gel, eluted with 10% methanol/dichloromethane) yielded 1-({1-acetyl-4-[2-(methylsulfonyl)ethoxy]piperidin-4-yl}methyl)-2-(ethoxyethyl)-1H-imidazo[4,5-c]quinoline (0.30 g, 13%) and recovered starting material, 1-acetyl-4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidin-4-ol (1.20 g).

Workup

  1. customPurification
  2. washby flash chromatography (silica gel, eluted with 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-378ec050cd2246549b83a710d8971615
Source dataset
uspto-grants-2011_02
Patent number
US07884207B2

Reaction notes

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