Triethylamine → N-[4-(4H-Pyrazolo[5,1-c][1,4]benzodiazepin-5(10H)-ylcarbonyl)phenyl]-2-methylbenzamide

HRID 3537

Reaktionsgleichung

[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1)=[O:5].C(N(CC)CC)C.[N:27]1[N:36]2[C:30]([CH2:31][NH:32][C:33]3[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=3[CH2:35]2)=[CH:29][CH:28]=1>C(Cl)Cl.C(OCC)(=O)C>[N:27]1[N:36]2[C:30]([CH2:31][N:32]([C:11]([C:10]3[CH:14]=[CH:15][C:7]([NH:6][C:4](=[O:5])[C:3]4[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=4[CH3:1])=[CH:8][CH:9]=3)=[O:12])[C:33]3[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=3[CH2:35]2)=[CH:29][CH:28]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a mixture of 1.37 g of 4-[(2-methylbenzoyl)amino]benzoyl chloride in 15 ml of methylene chloride, cooled to 0° C. is added 1.5 ml of triethylamine. To the mixture is added 5 mmol of 5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine. The reaction mixture is allowed to stir at room temperature for 48 hours and the volatiles are removed in vacuo to give a residue. The residue is dissolved in 100 ml of ethyl acetate and washed with water, 2N citric acid, aqueous NaHCO3 and brine. The solution is dried with Na2SO4 and the solvent removed in vacuo. The residue is purified by flash chromatography on silica gel with ethyl acetate-hexane to give the desired product, m.p. 142°-146° C.

Aufarbeitung

customthe volatiles are removed in vacuo
customto give a residue
washwashed with water, 2N citric acid, aqueous NaHCO3 and brine
dry with materialThe solution is dried with Na2SO4
customthe solvent removed in vacuo
customThe residue is purified by flash chromatography on silica gel with ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag: ord-640af18f5f2a4182aa628a6af14296b2
Quelldatensatz: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05733905

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