Potassium Carbonate → 7-benzyloxy-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline

HRID 540926Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

N-{7-(Benzyloxy)-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]quinolin-3-yl}propanamide dihydrochloride (14.2 g, 31.1 mmol) was slurried in ethanol (150 mL) and diluted with water (50 mL). Potassium carbonate (12.3 g, 89 mmol) in water (15 mL) was added and the reaction was stirred until dissolution (˜30 minutes). The reaction was then heated to 60° C. for 16 hours. The ethanol was evaporated under reduced pressure and the remaining water was extracted with dichloromethane. The organic fraction was sequentially washed with water, followed by saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated. Recrystallization from acetonitrile afforded 8.4 g of 7-(benzyloxy)-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline as a tan powder.

Workup

customThe ethanol was evaporated under reduced pressure
extractionthe remaining water was extracted with dichloromethane
washThe organic fraction was sequentially washed with water
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customRecrystallization from acetonitrile

Sources & evidence

ORD record: ord-9cdc64ec74984d4b8a320fea08568f6f
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871782B2

Reaction notes

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