1-Fluoro-4-(methylsulphonyl)benzene → HCID 67778059, Verbindung

HRID 1039106

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:16][CH:15]3[CH2:17][CH2:18][NH2:19])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.F[C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1.C1CCN2C(=NCCC2)CC1>CN1C(=O)CCC1.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:16][CH:15]3[CH2:17][CH2:18][NH:19][C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

2-{2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanamine from step 3 of this example (50 mg, 0.178 mmol) was in 0.594 mL NMP. 1-fluoro-4-(methylsulfonyl)benzene (37.2 mg, 0.2141 mol) and DBU (0.040 mL, 0.267 mmol) were sequentially added. The reaction mixture was stirred at 110° C. overnight before cooled back to room temperature. The reaction mixture was diluted with water and aqueous phase was further extracted with ethyl acetate for 3 times. The combined organic layers were washed with water and brine, then dried over Na2SO4 and concentrated. The residue was purified by column chromatography using gradient elution (0 to 65% ethyl acetate in hexane) to give the titled compound. LRMS calc: 434.9; obs: 435 (M+1).

Aufarbeitung

temperaturebefore cooled back to room temperature
extractionwas further extracted with ethyl acetate for 3 times
washThe combined organic layers were washed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was purified by column chromatography
washelution (0 to 65% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag: ord-0deac29ef3874f8fba2af49edc399877
Quelldatensatz: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08552022B2

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