Pyridine → HCID 57515423, compound

HRID 44739Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:8][CH2:9][C:10]1[N:11]([CH2:23][C:24]2([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[C:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=1)[CH3:7].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:6]([O:8][CH2:9][C:10]1[N:11]([CH2:23][C:24]2([NH:30][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[C:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=1)[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Methanesulfonyl chloride (0.75 mL, 9.75 mmol) was added to a 0° C. solution of 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanamine (2.75 g, 8.13 mmol), 4-dimethylaminopyridine (DMAP, 2.75 g) and pyridine (11 mL) in dichloromethane (28 mL). The solution was stirred at 0° C. for 2 h, then at rt for 1 h. The reaction was washed with water (100 mL). The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure to yield a light yellow oil. Purification by flash chromatography (silica gel, 20% methanol/ethyl acetate) afforded N-(1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexyl)methanesulfonamide as a white solid (2.72 g, 80%).

Workup

waitat rt for 1 h
washThe reaction was washed with water (100 mL)
dry with materialThe organic phase was dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customto yield a light yellow oil
customPurification by flash chromatography (silica gel, 20% methanol/ethyl acetate)

Sources & evidence

ORD record: ord-89b7e4c14514457996b170f6572b319f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541438B2

Reaction notes

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