Triethylamine → 7,8-dimethoxy-(10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-(4-bromo-3-methyl-phenyl)-methanone

HRID 2184451Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2184451
[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[NH:12][CH2:11][C:10]3=[CH:13][CH:14]=[CH:15][N:9]3[CH2:8][C:7]=2[CH:16]=1.[CH3:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[Br:29])[C:23](Cl)=[O:24].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[N:12]([C:23]([C:22]3[CH:26]=[CH:27][C:28]([Br:29])=[C:20]([CH3:19])[CH:21]=3)=[O:24])[CH2:11][C:10]3=[CH:13][CH:14]=[CH:15][N:9]3[CH2:8][C:7]=2[CH:16]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 3108382,3-dimethoxy-6,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepineHCID 70215344-Bromo-3-methylbenzoyl chloride

Produkt 1

HCID 219477397,8-dimethoxy-(10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-(4-bromo-3-methyl-phenyl)-methanoneAusbeute 60,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 7,8-dimethoxy-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine of Step B (3.20 g) in dichloromethane (20 mL) was added 3-methyl-4-bromo benzoyl chloride (3.4 g, 1.1 equiv) and triethylamine (2.0 g, 1.5 equiv) and the mixture was stirred at room temperature overnight. The solvent was then removed in vacuo and the residue chromatographed on silica gel eluting with a solvent gradient from 5 to 50% ethyl acetate in petroleum ether to provide the title compounds as a yellow crystalline solid (3.5 g), m.p. 165-168° C.

Aufarbeitung

  1. customThe solvent was then removed in vacuo
  2. customthe residue chromatographed on silica gel eluting with a solvent gradient from 5 to 50% ethyl acetate in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-fc24d08677fe4dde9b9c203b70e41e72
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900200B2

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