Triethylamine → HCID 23502835, Verbindung

HRID 1835358Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1835358
C(Cl)(=O)C(Cl)=O.[F:7][C:8]([F:46])([F:45])[C:9]1[CH:10]=[C:11]([CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:40]=1)[CH2:12][N:13]([CH3:37])[C:14](=[O:36])[C:15]1[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])=[CH:19][C:18]([CH:28]([OH:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:17][CH:16]=1.C(N(CC)CC)C>ClCCl>[C:28]([C:18]1[CH:19]=[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[C:15]([C:14]([N:13]([CH2:12][C:11]2[CH:10]=[C:9]([C:8]([F:45])([F:7])[F:46])[CH:40]=[C:39]([C:41]([F:43])([F:44])[F:42])[CH:38]=2)[CH3:37])=[O:36])=[CH:16][N:17]=1)(=[O:35])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 23502874(RS)-N-(3,5-Bis-trifluoromethyl-benzyl)-6-(hydroxy-phenyl-methyl)-N-methyl-4-o-tolyl-nicotinamide

Produkt 1

HCID 23502835HCID 23502835, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 0.018 ml (0.21 mmol) oxalyl chloride in 2.5 ml dichloromethane 0.03 ml (0.4 mmol) dimethylsulfoxide were added at −78° C. After 5 min a solution of 100 mg (0.179 mmol) (RS)-N-(3,5-bis-trifluoromethyl-benzyl)-6-(hydroxy-phenyl-methyl)-N-methyl-4-o-tolyl-nicotinamide (Example 76) in 2.5 ml dichloromethane were added dropwise at −78° C. After stirring for another 30 min at −78° C. 0.15 ml (0.90 mmol) triethylamine were added. The reaction mixture was allowed to warm to room temperature. Dilution with dichloromethane was followed by washing with three portions of 1 M aqueous hydrochloric acid solution and one portion of a saturated aqueous solution of sodium bicarbonate. The organic layer was dried with sodium sulfate and concentrated. Column chromatography afforded 69 mg (70%) of the title compound as a light-yellow foam.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. washby washing with three portions of 1 M aqueous hydrochloric acid solution and one portion of a saturated aqueous solution of sodium bicarbonate
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-093c3a91eaf64e6287718c6284956923
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06770637B2

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