Triethylamine → HCID 22591451, Verbindung

HRID 1372894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1372894
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:13]([CH3:18])([CH3:17])[C:14](Cl)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:21][NH:22][C:23]1[CH:24]=[N:25][C:26]([N:37]2[CH2:42][CH2:41][S:40][CH2:39][CH2:38]2)=[CH:27][C:28]=1[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=1[CH3:36].C(N(CC)CC)C.[OH-].[Na+]>ClCCl>[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:13]([CH3:18])([CH3:17])[C:14]([N:22]([CH3:21])[C:23]2[CH:24]=[N:25][C:26]([N:37]3[CH2:38][CH2:39][S:40][CH2:41][CH2:42]3)=[CH:27][C:28]=2[C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=2[CH3:36])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 21072794HCID 21072794, Verbindung

Produkt 1

HCID 22591451HCID 22591451, VerbindungAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 8.5 g (26.6 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride in 12 ml dichloromethane was added dropwise at room temperature to a solution of 8.0 g (24.2 mmol) methyl-[4-(4-fluoro-2-methyl-phenyl)-6-thiomorpholin-4-yl-pyridin-3-yl]-amine and 4.7 ml (33.9 mmol) triethylamine in 65 ml dichloromethane. The reaction mixture was stirred for 1 hour and poured onto 50 ml 1 N aqueous sodium hydroxide. After extraction the phases were separated, the aqueous phase was extracted with dichloromethane and the organic phases were washed with water. The combined organic extracts were concentrated under reduced pressure and the solvent was exchanged for 150 ml ethanol. The solution was seeded at 40° C. with some crystals, 30 ml water were slowly added and the system was stirred for 1 hour at room temperature and for 1 hour at 0° C. The precipitate was filtered off, washed with cold ethanol (0° C.) and dried under high vacuum to yield 13.0 g (76% over 3 steps) 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-[4-(4-fluoro-2-methyl-phenyl)-6-thiomorpholin-4-yl-pyridin-3-yl]-isobutyramide as an off-white powder of

Aufarbeitung

  1. extractionAfter extraction the phases
  2. customwere separated
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. washthe organic phases were washed with water
  5. concentrationThe combined organic extracts were concentrated under reduced pressure
  6. customwas seeded at 40° C. with some crystals, 30 ml water
  7. additionwere slowly added
  8. stirringthe system was stirred for 1 hour at room temperature and for 1 hour at 0° C
  9. filtrationThe precipitate was filtered off
  10. washwashed with cold ethanol (0° C.)
  11. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e2ca6360827f46f1a02484195bb4c684
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07160881B2

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