Water → HCID 66733412, Verbindung

HRID 1184646

Reaktionsgleichung

Reaktionsgleichung von HRID 1184646
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([C:18]([N:20]2[C:26]3[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:25]=3[CH:24]([OH:32])[CH2:23][CH2:22][CH2:21]2)=[O:19])=[C:15]([CH3:17])[CH:16]=1)=[O:9].N1C=CC=CC=1.[Cl:39][CH2:40][CH2:41][CH2:42][C:43](Cl)=[O:44].O>ClCCl>[Cl:39][CH2:40][CH2:41][CH2:42][C:43]([O:32][CH:24]1[CH2:23][CH2:22][CH2:21][N:20]([C:18](=[O:19])[C:14]2[CH:13]=[CH:12][C:11]([NH:10][C:8](=[O:9])[C:7]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[CH3:1])=[CH:16][C:15]=2[CH3:17])[C:26]2[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:25]1=2)=[O:44]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 783704-Chlorobutyryl chlorideHCID 216237Tolvaptan

Produkt 1

HCID 66733412HCID 66733412, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Tolvaptan (10.0 g, 22.3 mmol) was dispersed in dichloromethane (100 ml). Pyridine (2.7 ml) was added thereto, and the mixture was stirred. 4-Chlorobutyric acid chloride (3.74 ml) was gradually added to the obtained mixture, and the mixture was stirred at room temperature over night. The reactant was then poured into water, and the mixture was extracted with dichloromethane, washed with a sodium hydrogen sulfate aqueous solution, dried over magnesium sulfate. After filtration and concentration under reduced pressure, the resulted residue was crystallized with diethyl ether. The resulted crystals were collected by filtration, and dried to obtain 10.7 g of 7-chloro-1-[2-methyl-4-(2-methylbenzamido)benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl 4-chlorobutyrate as white powder.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature over night
  2. extractionthe mixture was extracted with dichloromethane
  3. washwashed with a sodium hydrogen sulfate aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration and concentration under reduced pressure
  6. customthe resulted residue was crystallized with diethyl ether
  7. filtrationThe resulted crystals were collected by filtration
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-082eedab464b4964a3a154191056b482
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669229B2

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