Diisopropylethylamine → (S)-7-fluoro-2-trifluoromethyl-11-[3-(3-methoxy-propyl)-piperazin 1-yl]-5H-dibenzo[b,e][1,4]diazepine

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Reaktionsgleichung

Cl.[F:2][C:3]1[CH:22]=[CH:21][C:6]2[N:7]=[C:8]([NH2:20])[C:9]3[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:10]=3[NH:11][C:5]=2[CH:4]=1.[CH3:23][O:24][CH2:25][CH2:26][CH2:27][C@H:28]1[CH2:33]N[CH2:31][CH2:30][NH:29]1.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1.CS(C)=O>[F:2][C:3]1[CH:22]=[CH:21][C:6]2[N:7]=[C:8]([N:20]3[CH2:31][CH2:30][NH:29][C@@H:28]([CH2:27][CH2:26][CH2:25][O:24][CH3:23])[CH2:33]3)[C:9]3[CH:15]=[C:14]([C:16]([F:17])([F:19])[F:18])[CH:13]=[CH:12][C:10]=3[NH:11][C:5]=2[CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

Combine 7-fluoro-2-trifluoromethyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride (0.399 g, 1.20 mmol), (S)-2-(3-methoxy-propyl)-piperazine (0.381 g, 2.41 mmol), and diisopropylethyl amine (0.21 mL, 1.20 mmol) in a mixture of toluene (4.5 mL) and dimethylsulfoxide (1.5 mL) and stir at 110° C. for 24 hours. Evaporate the mixture then purify by flash chromatography, eluting with a step gradient starting with dichloromethane going to 7% 2N ammonia-methanol in dichloromethane gives (s)-7-fluoro-11-[3-(3-methoxy-propyl)-piperazin-1-yl]-2-trifluoromethyl-5H-dibenzo[b,e][1,4]diazepine (0.268 g, 0.614 mmol, 51%) as a yellow oil. Mass spectrum (APCI): m/z=437.2 (M+1).

Aufarbeitung

customEvaporate the mixture
customthen purify by flash chromatography
washeluting with a step gradient

Quellen und Nachweise

ORD-Eintrag: ord-e5e879f3567541a2bb3418a896305506
Quelldatensatz: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07384934B2

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