Cyclopentylamine → 4-(Cyclopentylamino)-7-fluoro-6-methoxy-3-quinolinecarbonitrile

HRID 1837333Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[CH:17]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18]1>C(OCCO)C>[CH:17]1([NH:22][C:2]2[C:11]3[C:6](=[CH:7][C:8]([F:14])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-7-fluoro-6-methoxy-3-quinolinecarbonitrile (400 mg, 1.69 mmol) and cyclopentylamine (307 mg, 3.72 mmol) in 11 mL of 2-ethoxyethanol is heated at 100° C. for 1.5 hours then cooled to room temperature. The reaction mixture is concentrated in vacuo and aqueous sodium bicarbonate is added to the residue. After stirring for 20 minutes, the solids are collected by filtration. Purification by preparative thin layer chromatography, eluting with 5% methanol in dichloromethane, followed by trituration with diethyl ether and hexane, provides 359 mg of 4-cyclopentylamino-7-fluoro-6-methoxy-3-quinolinecarbonitrile, mp 162-164° C.

Workup

temperaturethen cooled to room temperature
concentrationThe reaction mixture is concentrated in vacuo and aqueous sodium bicarbonate
additionis added to the residue
filtrationthe solids are collected by filtration
customPurification by preparative thin layer chromatography
washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record: ord-48cf27b7386847caae743d000ba720c3
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780996B2

Reaction notes

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