Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | N-Methyl-3-pyridinamine | HCID 140376 | — |
| Reactant | 2,5-Dichlorothiophene-3-carboxylic acid | HCID 225438 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66801152 | HCID 66801152 | 64.6% |
Reaction Steps
394 mg (2.0 mmol, 1.0 equiv.) of 2,5-dichloro-thiophene-3-carboxylic acid were dissolved in 8 ml of dichloromethane and 254 mg (2.0 mmol, 1.0 equiv.) of oxalyl chloride were added dropwise. A catalytic amount of N,N-dimethylformamide (DMF) (5 drops) was added and the reaction mixture was stirred at room temperature for 4 h. Then, the mixture was added dropwise to a solution of 300 mg (3.0 mmol, 1.5 equiv) of triethylamine and 217 mg (2.0 mmol, 1.0 equiv.) of methyl-pyridin-3-yl-amine in 6 ml of dichloromethane and the reaction was stirred at room temperature overnight. Water was added and the mixture was extracted with dichloromethane. The combined organic phases were dried over Na2SO4, filtered and the solvent was removed under reduced pressure to yield 371 mg of the title compound (65%, 95% purity), [Mt]: 288.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08609700B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-62ad0c33544243689ecf81a814f1c5a1 |
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| Source note | uspto-grants-2013_12 |
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