Triethylamine → HCID 178495799, Verbindung

To a solution of the product of Example 126A (0.20 g, 1.1 mmol) and Et3N (0.3 mL, 2.2 mmol) in 25 mL THF was added 2-bromobenzoyl chloride (Aldrich, 0.18 mL, 1.4 mmol). This mixture stirred at ambient temperature for 20 hours then was concentrated under reduced pressure and the residue was diluted with 10 mL EtOAc and washed with 5 mL NH4Cl. The layers were separated and the aqueous layer was extracted (2×5 mL EtOAc). The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via recrystallization with 50% hexanes/EtOAc to afford 0.18 g of the title compound (0.49 mmol, 46% yield). 1H NMR (300 MHz, CDCl3) δ ppm 2.26 (s, 3H), 2.28 (s, 3H), 3.30 (s, 3H), 3.78 (t, J=5.1 Hz, 2H), 4.42 (t, J=5.1 Hz, 2H), 7.22 (dt, J=7.8, 1.7 Hz, 1H), 7.34 (dt, J=7.5, 1.4 Hz, 1H), 7.63 (dd, J=8.0, 1.2 Hz, 1H), 7.90 (dd, J=7.6, 1.9 Hz, 1H); MS (DCI/NH3) m/z 369, 371 (M+H)+; Anal. calculated for C15H17BrN2O2S: C, 48.79; H, 4.64; N, 7.59. Found: C, 48.84; H, 4.49; N, 7.40.

1. concentrationthen was concentrated under reduced pressure
2. additionthe residue was diluted with 10 mL EtOAc
3. washwashed with 5 mL NH4Cl
4. customThe layers were separated
5. extractionthe aqueous layer was extracted (2×5 mL EtOAc)
6. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. custompurified via recrystallization with 50% hexanes/EtOAc

ORD-Eintrag

ord-2f5326c079814a9aa88858ec680cb96d

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08546583B2