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

HRID 2203601Notes

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-f22db1714ce14202abb3b72252015660
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365567B2

Reaction notes

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