Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Methylpiperazine | HCID 53167 | — |
| Reactant | HCID 59631668 | HCID 59631668 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | HCID 59633401 | HCID 59633401 | 54.2% |
Reaction Steps
Triethylamine (0.15 mL, 1.1 mmol) and a small amount of DMAP were dissolved in 1,2-dichloroethane (2 mL) in a reaction vial. This solution was treated with 1-methyl piperazine (50 μL, 0.45 mmol) followed by 5-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophene-2-sulfonyl chloride (145 mg, 0.34 mmol) as a solution in 1,2-dichloroethane (1 mL). After stirring 4½ hours at ambient temperature the reaction was quenched by dilution with CH2Cl2 and water. Saturated NaHCO3 was added and the basic aqueous was extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to afford crude product as a pale yellow oil. This crude product was purified by flash column chromatography eluting with a gradient from CH2Cl2 to 16% acetonitrile/CH2Cl2 to afford 1-(5-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophen-2-ylsulfonyl)-4-methylpiperazine (90.5 mg, 54% yield) as a brittle white foam. MS(ES): 491 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08703805B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-c81f194379934c20a764f568bc58a7bb |
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| Source note | uspto-grants-2014_04 |
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