alpha-Bromo-o-chlorotoluene → N-[(2-Chlorophenyl)methyl]-N-[4-(5H-pyrrolo(2,1-c]-[1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl)-4-morpholineacetamide

HRID 3598

Reaktionsgleichung

Reaktionsgleichung von HRID 3598
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:32])[CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[CH:19][CH:18]=3)=[O:16])[CH2:6][C:5]=12.[CH:33]1[CH:38]=[C:37]([CH2:39]Br)[C:36]([Cl:41])=[CH:35][CH:34]=1.[H-].[Na+]>C(#N)C.O>[Cl:41][C:36]1[CH:35]=[CH:34][CH:33]=[CH:38][C:37]=1[CH2:39][N:23]([C:20]1[CH:19]=[CH:18][C:17]([C:15]([N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:16])=[CH:22][CH:21]=1)[C:24](=[O:32])[CH2:25][N:26]1[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1

Komponenten

6

Edukt 3

HCID 11905alpha-Bromo-o-chlorotoluene2×HCID 24758Sodium hydrideHCID 70059534N-[4-(5H-pyrrolo-[2,1-c][1,4]benzodiazepin10(11H)-ylcarbonyl)phenyl]4-morpholineacetamide

Produkt 1

HCID 15340681N-[(2-Chlorophenyl)methyl]-N-[4-(5H-pyrrolo(2,1-c]-[1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl)-4-morpholineacetamideAusbeute 126,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 0.11 g of N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-4-morpholineacetamide, 56 mg of O-chlorobenzyl bromide and 0.41 g of K2 CO3 in 5 ml of acetonitrile is heated at reflux for 18 hours. An additional 30 mg of O-chlorobenzyl bromide and 0.4 mmol of sodium hydride is added followed by heating for 24 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The organic layer is dried with Na2SO4 and evaporated to give 0.18 g of a residue which is purified by chromatography on silica gel with 1:1 ethyl acetate-methylene chloride to give 80 mg of off white solid. MS(CI): 555 (M+H).

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 18 hours
  3. temperatureby heating for 24 hours
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer is dried with Na2SO4
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0377322d180742a7acad3e33e6f3f423
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733905

Verknüpfte Notizen

Wird geladen…