Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | [6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]carboxylic acid | HCID 23114724 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 23114664 | HCID 23114664 | 90% |
Reaction Steps
After the [6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]carboxylic acid (90 mg, 0.21 mmol) obtained in Example 338, a tetrahydrofuran solution (2.0M, 0.21 ml, 0.42 mmol) of dimethylamine, 4-(dimethylamino)pyridine (15 mg, 0.12 mmol) and triethylamine (0.045 ml, 0.32 mmol) were dissolved in dichloromethane (5 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (61 mg, 0.32 mmol) was added to the resulting solution at room temperature. The resulting mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography and a fraction obtained from the elution portion with hexane:ethyl acetate=2:1 was concentrated under reduced pressure, whereby the title compound (35 mg, 0.066 mmol, 90%) was obtained as a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07399775B2 |
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| Source dataset | uspto-grants-2008_07 |
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| ORD ID | ord-5c339159cb474003b16b6c24a7da9b43 |
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| Source note | uspto-grants-2008_07 |
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