(S)-2-(2-Methoxyethyl)piperazine → (S)-7-Chloro-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene

HRID 131457

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

Dissolve 7-chloro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride (1.46 g, 4.86 mmol) and (S)-2-(2-methoxy-ethyl)-piperazine (2.1 g, 14.6 mmol) in dimethylsulfoxide/toluene (1:2)(18 ml), stir under nitrogen and heat in an oil bath at 130° C. for 28.5 hours. Stir 16 hours at ambient temperature. Dilute the mixture with water and ethyl acetate, and extract with ethyl acetate. Combine the ethyl acetate extracts, wash with water and brine, dry the organic phase (Na2SO4), filter and concentrate under reduced pressure. Chromatograph on silica gel (eluent: 0-10% 2N ammonia in methanol/dichloromethane) to give the title compound (1.14 g, 60%), Mass Spectrum (ESMS) 391/393 (M+1), mp 179-183° C. (dec).

Workup

stirringStir 16 hours at ambient temperature
extractionextract with ethyl acetate
washwash with water and brine
dry with materialdry the organic phase (Na2SO4)
filtrationfilter
concentrationconcentrate under reduced pressure

Sources & evidence

ORD record: ord-0de79bc9bdcf4decb9130433baa099b5
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Linked notes

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