2,6-Lutidine → N-((1-(2-(1-methylethylsulfonamido)ethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide
Reaktionsgleichung
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][NH:11][C:12](=[O:27])[C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=2)[CH2:6][CH2:5]1.N1C(C)=CC=CC=1C.[CH:36]([S:39](Cl)(=[O:41])=[O:40])([CH3:38])[CH3:37].C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH3:37][CH:36]([S:39]([NH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([CH2:10][NH:11][C:12](=[O:27])[C:13]2[CH:18]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:16]=[C:15]([C:23]([F:24])([F:25])[F:26])[CH:14]=2)[CH2:8][CH2:9]1)(=[O:41])=[O:40])[CH3:38]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- -20 °C
Versuchsvorschrift
A solution of N-((1-(2-aminoethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide (70 mg, 0.18 mmol) and 2,6-lutidine (123 μL, 0.882 mmol) in CH2Cl2 (2 mL) was treated with isopropylsulfonyl chloride (49.9 mg, 0.35 mmol). The reaction was stirred overnight and then transferred to a test tube containing saturated aqueous NaHCO3 (4 mL) and EtOAc (4 mL). The biphasic mixture was mixed vigourously and allowed to separate for 15 min. After separation, the mixture was cooled to −20° C. until the aqueous layer was frozen. The organic layer was then poured off and the solvent was removed under reduced pressure at 50° C. The resulting residue was purified by HiTOPs
Aufarbeitung
- customtransferred to a test tube
- additionThe biphasic mixture was mixed vigourously
- customto separate for 15 min
- customAfter separation
- temperaturewas frozen
- additionThe organic layer was then poured off
- customthe solvent was removed under reduced pressure at 50° C
- customThe resulting residue was purified by HiTOPs
Quellen und Nachweise
- ORD-Eintrag
- ord-a12308d317fc4170ade14dde01f2c21b
- Quelldatensatz
- uspto-grants-2015_08
- Patentnummer
- US09096522B2
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