4-(1-Pyrrolidinyl)piperidine → 4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-(4-pyrrolidin-1-ylpiperidin-1-yl)quinoline-3-carbonitrile

HRID 499128

Reaktionsgleichung

[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[C:21]([O:25][CH3:26])=[CH:20][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11](F)=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:18]#[N:19].[N:27]1([CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH2:31][CH2:30][CH2:29][CH2:28]1>CN1CCCC1=O>[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[C:21]([O:25][CH3:26])=[CH:20][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([N:35]3[CH2:36][CH2:37][CH:32]([N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)[CH2:33][CH2:34]3)=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:18]#[N:19]

Komponenten

Reaktionsbedingungen

Temperatur: 105 °C

Versuchsvorschrift

Following the procedure of Example 11, a mixture of 200.0 mg (0.51 mmol) of 4-(2,4-dichloro-5-methoxyanilino)-7-fluoro-6-methoxy-3-quinolinecarbonitrile and 472.0 mg (3.06 mmol) of 4-(1-pyrrolidinyl)piperidine in 1.0 mL of 1-methyl-2-pyrrolidinone is heated in a sealed tube at 105° C. for 15 hours to yield the crude product. Purification by preparative thin layer chromatography (eluting with 4:1 dichloromethane/methanol) provides 116.5 mg of the pure product as a yellow solid, mp 225-227° C.

Aufarbeitung

customto yield the crude product
customPurification
washby preparative thin layer chromatography (eluting with 4:1 dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag: ord-fc9509364c304179903a6caa4a7f434a
Quelldatensatz: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07767671B2

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