Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Ethanesulfonyl chloride | HCID 11667 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine | HCID 67340307 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 67340839 | HCID 67340839 | 22% |
Reaction Steps
Ethanesulfonyl chloride (0.024 g, 0.19 mmol) and then dichloromethane (0.5 mL) were added sequentially to a mixture of diisopropylethylamine (0.044 g, 0.34 mmol) and 6-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (0.050 g, 0.17 mmol) in toluene (1.5 mL). The reaction mixture was stirred for 1 hour at ambient temperature and then for 1.5 hours at 50° C. and then evaporated to give an involatile residue. The residue was purified by preparative hplc using a Phenomenex Luna C18 100A column (10μ silica, 21 mm diameter, 150 mm length) eluted with decreasingly polar mixtures of water (containing 0.1% trifluoroacetic acid) and acetonitrile as eluents to give 6-(5-ethylsulfonyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-2-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[3,4-f]pyridazine (0.0143 g, 22%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08003649B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-c085b281666e4abf9b0edbc2534b34a0 |
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| Source note | uspto-grants-2011_08 |
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