Reaktionsgleichung
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=3)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22](O)(=[O:25])[CH:23]=[CH2:24].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.N1(C2C=CN=CC=2)CCCC1>ClCCl>[C:1]1([S:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:16]=[C:17]([NH:21][C:22](=[O:25])[CH:23]=[CH2:24])[CH:18]=[CH:19][CH:20]=3)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a stirred solution of N1-(4-(phenylthio)pyrimidin-2-yl)benzene-1,3-diamine (80 mg, 0.27 mmol) and acrylic acid (37 μL, 0.54 mmol) in anhydrous dichloromethane (2 mL), was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride salt (78 mg, 0.41 mmol), triethylamine (114 μL, 0.82 mmol) and 4-pyrrolidinopyridine (5 mg). The resulting mixture was stirred at room temperature under nitrogen atmosphere for 16 hours. It was diluted with dichloromethane (20 mL), washed with water, 2.0 Maqueous sodium carbonate solution, and dried (Na2SO4). After removal of the solvent in vacuo, the residue was flash chromatographed on silica gel using ethyl acetate:petroleum ether (50:50→100:0) as eluant to give the desired product (31 mg, 33%).
Aufarbeitung
- washwashed with water, 2.0 Maqueous sodium carbonate solution
- dry with materialdried (Na2SO4)
- customAfter removal of the solvent in vacuo
- customchromatographed on silica gel
Quellen und Nachweise
- ORD-Eintrag
- ord-8ed5f0d69e874edf8a480bbff42c6d10
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- US08846704B2
Verknüpfte Notizen
Wird geladen…