HCID 86052868, compound → HCID 86612250, compound

HRID 1623120Notes

Reaction equation

HRID 1623120 reaction equation
[CH3:1][O:2][N:3]=[C:4]([CH2:6][CH2:7][CH2:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=[C:10]1[CH2:22][CH2:23][CH3:24])[CH3:5].CON=CCCCN1C2C3C=CC=CC=3N=CC=2N=C1CCC>>[CH3:1][O:2][NH:3][CH:4]([CH3:5])[CH2:6][CH2:7][CH2:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=[C:10]1[CH2:22][CH2:23][CH3:24]

Participants

3

Reactant 2

HCID 86052868HCID 86052868, compoundHCID 86612251HCID 86612251, compound

Product 1

HCID 86612250HCID 86612250, compoundYield 60.7%

Procedure

A modification of the general procedure of Part E of Example 6 was followed to treat 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one O-methyloxime (4.6 g, 14.17 mmol) in lieu of 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde O-methyloxime. Purification with flash column chromatography on silica gel (eluting with 5% methanol in dichloromethane) afforded 2.81 g of O-methyl-N-[1-methyl-4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]hydroxylamine.

Workup

  1. customPurification with flash column chromatography on silica gel (eluting with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0225f0e4c65246bcb34e7dd900c1724e
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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