Hydrochloric Acid → N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamide

HRID 2217790Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]([NH2:12])=[C:7]([Cl:13])[CH:6]=[CH:5][C:4]=2[N:3]=1.[CH:14]1([CH2:20][C:21](O)=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl>CN1CCCC1=O.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:13])[C:8]=2[NH:12][C:21](=[O:22])[CH2:20][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 2,6-dichloroquinolin-5-amine (prepared as described in (d) below) (1 g) in N-methylpyrrolidinone (12 mL) was added 4-N,N-dimethylaminopyridine (1.2 g), cyclohexaneacetic acid (1 g) and PyBroP (4.4 g). The reaction mixture was heated to 50° C. for 10 hours. The mixture was cooled to room temperature and poured into water (10 mL) which was subsequently acidified to pH1 with aqueous 2M hydrochloric acid. The resulting solution was extracted with dichloromethane (3×20 mL). The combined organic extracts were dried, filtered and partially concentrated to give a white precipitate which was removed by filtration. Purification by chromatography (SiO2, methanol:dichloromethane 1:10 as eluant) gave the sub-title compound (490 mg).

Workup

temperatureThe mixture was cooled to room temperature
extractionThe resulting solution was extracted with dichloromethane (3×20 mL)
customThe combined organic extracts were dried
filtrationfiltered
concentrationpartially concentrated
customto give a white precipitate which
customwas removed by filtration
customPurification by chromatography (SiO2, methanol:dichloromethane 1:10 as eluant)

Sources & evidence

ORD record: ord-19cfd7d851094c0c82813bd73c58e3bb
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

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