Diisopropylethylamine → (S)-9-Fluoro-5-[3-phenethyl-piperazine-1-yl]-11H-12-thia-6,11-diaza-dibenzo[a,f]azulene

HRID 1350486Notes

Reaction equation

Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:15]=[C:14]([NH2:16])[C:13]3[C:12]4[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=4[S:10][C:9]=3[NH:8][C:7]=2[CH:21]=1.[CH2:22]([C@H:30]1[CH2:35]N[CH2:33][CH2:32][NH:31]1)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.C1(C)C=CC=CC=1.C(Cl)Cl>[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:15]=[C:14]([N:16]3[CH2:33][CH2:32][NH:31][C@@H:30]([CH2:22][CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH2:35]3)[C:13]3[C:12]4[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=4[S:10][C:9]=3[NH:8][C:7]=2[CH:21]=1

Participants

Conditions

Temperature: 115 °C

Procedure

Combine 9-fluoro-11H-12-thia-6,11-diaza-dibenzo[a,f]azulen-5-ylamine hydrogen chloride (287 mg, 0.9 mmol), (S)-2-phenethyl-piperazine (340 mg, 1.80 mmol) and diisopropylethyl amine (116 mg, 0.9 mmol) in DMSO (0.5 mL) and toluene (2.0 mL), stir and microwave (300 W, 125 ° C.) for 8 h, then heat to 115 ° C. for 22 h. Cool the reaction to RT, dilute with CH2Cl2, wash with H2O and brine. Dry the organic layer with by Na2SO4. The crude material purify by chromatography on silica gel, gradient (100% CH2Cl2 to 100% CH2Cl2:2N NH3/MeOH=25:1), give 137 mg of title compound.

Workup

temperatureCool
customthe reaction to RT
washwash with H2O and brine
dry with materialDry the organic layer with by Na2SO4
customThe crude material purify by chromatography on silica gel, gradient (100% CH2Cl2 to 100% CH2Cl2:2N NH3/MeOH=25:1)

Sources & evidence

ORD record: ord-8d1e6ef4da8247849abf56d6c85f1e8f
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214673B2

Reaction notes

Loading…