Pyridine → {7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl}hexadecanoate

HRID 1626030

Reaktionsgleichung

Reaktionsgleichung von HRID 1626030
[C:1](Cl)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].ClCCl.[CH3:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=1[C:29]([NH:31][C:32]1[CH:33]=[CH:34][C:35]([C:39]([N:41]2[C:47]3[CH:48]=[CH:49][C:50]([Cl:52])=[CH:51][C:46]=3[CH:45]([OH:53])[CH2:44][CH2:43][CH2:42]2)=[O:40])=[C:36]([CH3:38])[CH:37]=1)=[O:30].N1C=CC=CC=1>O>[C:1]([O:53][CH:45]1[CH2:44][CH2:43][CH2:42][N:41]([C:39](=[O:40])[C:35]2[CH:34]=[CH:33][C:32]([NH:31][C:29](=[O:30])[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:22])=[CH:37][C:36]=2[CH3:38])[C:47]2[CH:48]=[CH:49][C:50]([Cl:52])=[CH:51][C:46]1=2)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 8206Palmitoyl chlorideHCID 216237Tolvaptan

Produkt 1

HCID 86652151{7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl}hexadecanoateAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Palmitoyl chloride (1.24 ml, 4.4 mmol) was added to a dichloromethane (20 ml) solution of tolvaptan (2.00 g, 4.4 mmol) and pyridine (0.40 ml, 5.0 mmol), and the mixture was stirred at room temperature over night. Water was added to the reaction mixture and the mixture was extracted with dichloromethane. The combined organic layer was washed with water and an aqueous saturated sodium chloride solution, and dried over magnesium sulfate. After filtration and concentration, the residue was purified by silica gel chromatography (n-hexane:ethyl acetate) to thereby obtain 2.25 g (74%) of {7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl} hexadecanoate as amorphous.

Aufarbeitung

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe combined organic layer was washed with water
  3. dry with materialan aqueous saturated sodium chloride solution, and dried over magnesium sulfate
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by silica gel chromatography (n-hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c42dfcfd72774ff4b76c371b67afaf58
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785386B2

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