2-{2-[2-ethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]ethenyl}-1H-isoindole-1,3(2H)-dione → 2-{2-[2-ethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]ethyl}-1H-isoindole-1,3(2H)-dione

HRID 244866Notes

Reaction equation

[CH2:1]([C:3]1[N:4]([CH2:29][C:30]([OH:33])([CH3:32])[CH3:31])[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([CH:15]=[CH:16][N:17]4[C:25](=[O:26])[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[C:18]4=[O:27])=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:28]=1)[CH3:2]>[Pd].CO>[CH2:1]([C:3]1[N:4]([CH2:29][C:30]([OH:33])([CH3:32])[CH3:31])[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([CH2:15][CH2:16][N:17]4[C:25](=[O:26])[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[C:18]4=[O:27])=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:28]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A glass Parr vessel was charged with 10% palladium on carbon (0.4 g), methanol (75 mL) and 2-{2-[2-ethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]ethenyl}-1H-isoindole-1,3(2H)-dione (1.9 g, 4.3 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 18 hours and then cooled to ambient temperature. The reaction mixture was filtered followed by concentration under reduced pressure to provide 1.9 g of 2-{2-[2-ethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]ethyl}-1H-isoindole-1,3(2H)-dione as a bright yellow solid. MS (APCI) m/z 443 (M+H)+.

Workup

customThe vessel was evacuated
additioncharged with hydrogen gas (40 psi, 2.8×105 Pa)
temperaturecooled to ambient temperature
filtrationThe reaction mixture was filtered
concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record: ord-ea729c8e380a40c387e995ba28b71452
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658666B2

Reaction notes

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