3-[2-ethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylprop-2-enamide → 3-[2-ethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylpropanamide

HRID 244837Notes

Reaction equation

[CH2:1]([C:3]1[N:4]([CH2:23][C:24]([OH:27])([CH3:26])[CH3:25])[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([CH:15]=[CH:16][C:17]([N:19]([CH3:21])[CH3:20])=[O:18])=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:22]=1)[CH3:2]>[Pd].CO>[CH2:1]([C:3]1[N:4]([CH2:23][C:24]([OH:27])([CH3:26])[CH3:25])[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([CH2:15][CH2:16][C:17]([N:19]([CH3:21])[CH3:20])=[O:18])=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:22]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A glass Parr vessel was charged with 10% palladium on carbon (0.14 g), methanol (50 mL) and 3-[2-ethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylprop-2-enamide (1.20 g, 3.27 mmol). The vessel was evacuated and charged with hydrogen gas (40 psi, 2.8×105 Pa). The reaction was shaken at 50° C. for approximately 19 hours. After cooling to ambient temperature, the reaction mixture was filtered and the filtrate concentrated to dryness to provide crude 3-[2-ethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylpropanamide as a white semi-solid. MS (APCI) m/z 369 (M+H)+.

Workup

customThe vessel was evacuated
additioncharged with hydrogen gas (40 psi, 2.8×105 Pa)
temperatureAfter cooling to ambient temperature
filtrationthe reaction mixture was filtered
concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record: ord-91fc2a65bf564eaba544a1448aeaaeeb
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658666B2

Reaction notes

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