p-Toluenesulfonic acid → 5-(5-Chlorobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([NH:17][CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[C:14]([CH:16]=3)[NH2:15])=[N:7][C:6]=2[CH:24]=1.[C:25]1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(OCC)(OCC)OCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]4[N:17]([CH:18]5[CH2:19][CH2:20][O:21][CH2:22][CH2:23]5)[CH:25]=[N:15][C:14]=4[CH:16]=3)=[N:7][C:6]=2[CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a solution of 5-chloro-2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole (see Working Example 100-2) (300 mg, 0.873 mmol) in triethyl orthoformate (5 mL) was added p-toluenesulfonic acid (10 mg), and this was stirred at 100° C. for 2 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution was added, and this was extracted with chloroform. The organic layer obtained was dried over anhydrous sodium sulfate, filtered, and concentrated to give crude crystals that were washed with diethyl ether and ethyl acetate to yield the title compound (200 mg, 65% yield) as brown crystals.

Aufarbeitung

extractionthis was extracted with chloroform
customThe organic layer obtained
dry with materialwas dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customto give crude crystals that
washwere washed with diethyl ether and ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-09f796d2475c447cb2318cc45d917e92
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08829035B2

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