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

HRID 853485Notes

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 brine 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 brine 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-3adcbabb7e8042128c1816a631a1b720
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253286B2

Reaction notes

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