Reaktionsgleichung
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=O)[CH3:10])[CH:5]=[N:4][CH:3]=1.[CH3:20][C:21]1[CH:22]=[C:23]([NH2:27])[CH:24]=[N:25][CH:26]=1.Cl.CN(C)CCCN=C=NCC.N1(C2C=CN=CC=2)CCCC1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([NH:27][C:23]2[CH:24]=[N:25][CH:26]=[C:21]([CH3:20])[CH:22]=2)=[O:16])[CH3:10])[CH:5]=[N:4][CH:3]=1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of 3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}benzoic acid (11 mg, 0.04 mmol), 5-methylpyridin-3-amine (5 mg, 0.048 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (11 mg, 0.059 mmol), 4-pyrrolidinopyridine (1.2 mg, 0.008 mmol) and triethylamine (0.013 mL, 0.095 mmol) in dichloromethane (1 mL) was stirred at room temperature for 17 hours. After this time the mixture was diluted with dichloromethane (20 mL), washed successively with saturated aqueous sodium hydrogen carbonate (2×15 mL) and brine (15 mL), dried (Na2SO4) and concentrated under reduced pressure to give a dark yellow oil which was purified by flash chromatography (silica, ethyl acetate/methanol) to give 3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}-N-(5-methylpyridin-3-yl)benzamide (9 mg, 61%) as a pale yellow oil.
Aufarbeitung
- washwashed successively with saturated aqueous sodium hydrogen carbonate (2×15 mL) and brine (15 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated under reduced pressure
- customto give a dark yellow oil which
- customwas purified by flash chromatography (silica, ethyl acetate/methanol)
Quellen und Nachweise
- ORD-Eintrag
- ord-54eb7710c91b4e22b485ec28d903e918
- Quelldatensatz
- uspto-grants-2015_05
- Patentnummer
- US09029386B2
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