Reaction equation
[C:1]([O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23](F)[CH:22]=[C:21]3[C:16]=2[C:17](=[O:26])[NH:18][CH:19]=[N:20]3)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][CH2:36][OH:37])[CH2:30][CH2:29]1.CC(C)([O-])C.[K+]>COCCOCCOC.ClCCl.O>[NH3:8].[C:1]([O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([O:37][CH2:36][CH2:35][CH2:34][N:31]3[CH2:30][CH2:29][N:28]([CH3:27])[CH2:33][CH2:32]3)[CH:22]=[C:21]3[C:16]=2[C:17](=[O:26])[NH:18][CH:19]=[N:20]3)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 3
Product 2
Reagents, catalysts & solvents 3
Procedure
5-{[1-(2-tert-butoxyethyl)piperidin-4-yl]oxy}-7-fluoroquinazolin-4(3H)-one (5.45 mg, 1.5 mmol) in anhydrous diglyme (15 ml) was reacted with 3-(4-methylpiperazin-1-yl)propan-1-ol (474 mg, 3 mmol) in the presence of potassium tert-butoxide (11.77 g, 10 mmol) at 100° C. for 4 hours. The reaction mixture was diluted with dichloromethane (10 ml) and water (10 ml) and the pH adjusted to 7.7. The mixture was extracted several times with dichloromethane and the organic phase dried (magnesium sulphate), evaporated and the residue purified by chromatography on silica gel. Elution with dichloromethane:methanolic ammonia (9:1) yielded 5-{[1-(2-tert-butoxyethyl)piperidin-4-yl]oxy}-7-[3-(4-methylpiperazin-1-yl)propoxy]quinazolin-4(3H)-one (411 mg, 55% yield):
Workup
- extractionThe mixture was extracted several times with dichloromethane
- dry with materialthe organic phase dried (magnesium sulphate)
- customevaporated
- customthe residue purified by chromatography on silica gel
- washElution with dichloromethane
Sources & evidence
- ORD record
- ord-dbb39fb66c83498ea7f50391fc9ea242
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07402585B2
Linked notes
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