Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Butylamine | HCID 8007 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-benzotriazol-1-yl-tetramethyluronium | HCID 130500 | — |
| Reactant | HCID 69375012 | HCID 69375012 | — |
| Product | HCID 69375734 | HCID 69375734 | 41% |
Reaction Steps
To a solution of 3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2-phenyl-2-propenoic acid (100 mg, 0.3784 mmol.) in 2 ml of DMFd were added O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoborate (121.5 mg, 0.3784 mmol.), N-hydroxybenzotriazole (51.1 mg, 0.3784 mmol) and N,N-diisopropylethylamine (129.2 μl, 0.7568 mmol). After stirring at room temperature for 30 min., 34.5 μl (0.3784 mmol.) of n-butylamine were added and the obtained solution was stirred at room temperature, for 24 hours. The resulting mixture was concentrated by evaporation of the solvent in vacuo, the residue was diluted with dichloromethane washed with 1 N NaOH, 1 N HCl, brine, dried over sodium sulphate and evaporated. The residual solid was triturated with Et2O to afford 49 mg of the title compound as a white solid (yield 41%) m.p. 177-179° C. (dec.)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06486322B1 |
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| Source dataset | uspto-grants-2002_11 |
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| ORD ID | ord-793ca2fb071a4f5393c80aa6fde574b7 |
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| Source note | uspto-grants-2002_11 |
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