N-[2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]-N'-isopropylurea → N-{2-[2-(ethoxymethyl)-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N'-isopropylurea

HRID 540876Notes

Reaction equation

HRID 540876 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][C:23]([NH:26][C:27]([NH:29][CH:30]([CH3:32])[CH3:31])=[O:28])([CH3:25])[CH3:24])[C:20]([CH2:33][O:34][CH2:35][CH3:36])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1>[Pd].C(O)C>[CH2:35]([O:34][CH2:33][C:20]1[N:21]([CH2:22][C:23]([NH:26][C:27]([NH:29][CH:30]([CH3:31])[CH3:32])=[O:28])([CH3:25])[CH3:24])[C:13]2[C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:19]=1)[CH3:36]

Participants

4

Reactant 1

HCID 67051122N-[2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]-N'-isopropylurea

Product 1

HCID 136347849N-{2-[2-(ethoxymethyl)-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N'-isopropylureaYield 101.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-{2-[7-(benzyloxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N′-isopropylurea (3.82 g, 7.80 mmol) and 10% palladium on carbon (0.92 g) in ethanol (100 mL) was hydrogenated at 50 psi (3.5×105 Pa) overnight on a Parr apparatus. The mixture was filtered through CELITE filter agent and the filtrate was concentrated under reduced pressure to yield 3.17 g of N-{2-[2-(ethoxymethyl)-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N′-isopropylurea as a yellow solid.

Workup

  1. customwas hydrogenated at 50 psi (3.5×105 Pa) overnight on a Parr apparatus
  2. filtrationThe mixture was filtered through CELITE
  3. filtrationfilter agent
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-813a727731434d009ce8a131658787d2
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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