m-Chloroperbenzoic acid → tert-butyl {4-[7-benzyloxy-2-(2-methoxyethyl)-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl]butyl}carbamate

HRID 598285Notes

Reaction equation

HRID 598285 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:20]([CH2:34][CH2:35][O:36][CH3:37])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:45]C1C=CC2C3N(CC(C)C)C(C)=NC=3C=NC=2C=1)C1C=CC=CC=1.C1C=C(Cl)C=C(C(OO)=O)C=1>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:30])[CH3:31])[C:20]([CH2:34][CH2:35][O:36][CH3:37])=[N:19][C:14]=3[CH:15]=[N+:16]([O-:45])[C:17]=2[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 670509187-benzyloxy-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolineHCID 86626159HCID 86626159, compound

Product 1

HCID 86626160tert-butyl {4-[7-benzyloxy-2-(2-methoxyethyl)-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl]butyl}carbamate

Procedure

A modification of the general method described in Part B of Example 3 was followed using tert-butyl {4-[7-benzyloxy-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}carbamate (9.08 g, 17.9 mmol) in lieu of 7-benzyloxy-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline. Over a period of 28 hours, three equivalents of mCPBA were added. Following the work-up procedure, 8.07 g of tert-butyl {4-[7-benzyloxy-2-(2-methoxyethyl)-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl]butyl}carbamate were obtained.

Sources & evidence

ORD record
ord-7a8f947867114efba1a75317001d164b
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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