Dimethylformamide → 4-(4-Amino-3-fluorophenoxy)-7-(1-methylpiperidin-3-ylmethoxy)quinoline-6-carbonitrile

HRID 387958Notes

Reaction equation

CN(C)C=O.Cl.Cl[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH3:15])[CH2:10]1.C(=O)([O-])[O-].[K+].[K+].[NH2:22][C:23]1[CH:42]=[CH:41][C:26]([O:27][C:28]2[C:37]3[C:32](=[CH:33][C:34]([OH:40])=[C:35]([C:38]#[N:39])[CH:36]=3)[N:31]=[CH:30][CH:29]=2)=[CH:25][C:24]=1[F:43]>C(OCC)(=O)C.O>[NH2:22][C:23]1[CH:42]=[CH:41][C:26]([O:27][C:28]2[C:37]3[C:32](=[CH:33][C:34]([O:40][CH2:8][CH:9]4[CH2:14][CH2:13][CH2:12][N:11]([CH3:15])[CH2:10]4)=[C:35]([C:38]#[N:39])[CH:36]=3)[N:31]=[CH:30][CH:29]=2)=[CH:25][C:24]=1[F:43]

Participants

Conditions

Temperature: 20 °C

Procedure

After adding dimethylformamide (4 ml), 3-chloromethyl-1-methylpiperidine hydrochloride (621 mg) and potassium carbonate (840 mg) to 4-(4-amino-3-fluorophenoxy)-6-cyano-7-hydroxyquinoline (400 mg), the mixture was stirred at 20° C. for 3 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, the organic layer was washed with water and saturated saline in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by NH silica gel column chromatography (ethyl acetate) to obtain the title compound (60 mg).

Workup

washthe organic layer was washed with water and saturated saline in that order
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe obtained crude product
customwas purified by NH silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-f2152a86cd90490a9ea71f590a261188
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372981B2

Reaction notes

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