HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 131517Generated: November 1, 2026
Diisopropylethylamine → (S)-9-Fluoro-5-[3-(2-methoxy-ethyl)-piperazine-1-yl]-11H-12-thia-6,11-diaza-dibenzo[a,f]azulene
https://huagongshe.com/reaction/131517
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 12-Amino-8-fluoro-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine hydrochloride | HCID 18422384 | — |
| Reactant | (S)-2-(2-Methoxyethyl)piperazine | HCID 55287560 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-9-Fluoro-5-[3-(2-methoxy-ethyl)-piperazine-1-yl]-11H-12-thia-6,11-diaza-dibenzo[a,f]azulene | HCID 10251015 | — |
Reaction Steps
Combine 9-fluoro-11H-12-thia-6,11-diaza-dibenzo[a,f]azulen-5-ylamine hydrogen chloride (510.2 mg, 1.6 mmol, (S)-2-(2-methoxy-ethyl) piperazine (460.8 mg, 3.2 mmol) and diisopropylethyl amine (206 mg, 1.6 mmol) in DMSO (0.75 mL) and toluene (3.0 mL), stir and heat to 110° C. After 55 hours, cool the reaction to RT, dilute with CH2Cl2, wash with H2O and Brine. Dry the organic layer with by Na2SO4. The crude material pass through a 5 g SCX column, collect the 0.2 N NH3/MeOH eluent, concentrate to a residue, which purified by chromatography on silica gel, gradient (100% CH2Cl2 to 100% CH2Cl2: 2N NH3/MeOH=15:1), give 410 mg of title compound. Mass spectrum: ACPI (m/e): 411.2 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07384934B2 |
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| Source dataset | uspto-grants-2008_06 |
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| ORD ID | ord-dd6e4b61d46f4ba6a7a67d3a610f9cf2 |
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| Source note | uspto-grants-2008_06 |
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