Potassium tert-butoxide → tert-butyl 10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

HRID 1364029Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]([CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=1.CC(C)([O-])C.[K+]>C1COCC1>[CH:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[C:5]1[N:4]3[CH2:16][CH2:17][N:18]([C:19]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:25])[CH2:2][C:3]3=[N:15][C:6]=1[CH:7]=[N:8]2

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere, a solution of tert-butyl 2-[2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamate (54.94 g, 152.3 mmol) in THF (400 mL) was cooled to 0° C.; a solution of potassium tert-butoxide (18.79 g of a 1 M solution in THF, 167.5 mmol) was added slowly. The reaction was stirred at 0° C. for three hours and then at ambient temperature overnight. The THF was removed under reduced pressure, and a 1:1 mixture of water and saturated aqueous sodium bicarbonate was added. The aqueous mixture was extracted with dichloromethane, and the combined extracts were washed sequentially with water and brine and concentrated under reduced pressure to provide 29.54 g of tert-butyl 10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate.

Workup

customat ambient temperature
customovernight
customThe THF was removed under reduced pressure
additiona 1:1 mixture of water and saturated aqueous sodium bicarbonate
additionwas added
extractionThe aqueous mixture was extracted with dichloromethane
washthe combined extracts were washed sequentially with water and brine
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-92518614a1b7468390f4471b6eb0dd21
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888349B2

Reaction notes

Loading…