Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 22179978 | HCID 22179978 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69591862 | HCID 69591862 | 33.1% |
Reaction Steps
A mixture of 3-benzyl-2-{1-[(3-tert-butoxycarbonylamino-propyl)-(4-methyl-benzoyl)-amino]-propyl}-4-oxo-3,4-dihydro-pyrrolo[2,1-f]-[1,2,4]triazine-5-carboxylic acid (0.0029 g, 0.0048 mmol), HOBt (0.0013 g, 0.0097 mmol), EDCI (0.002 g, 0.0097 mmol), dimethylamine (2 M in THF, 0.024 ml, 0.048 mmol) and DIPEA (0.003 mL, 0.019 mmol) in DMF (0.5 mL) were stirred at room temperature for 16 h. The reaction mixture was concentrated under vacuum, dissolved in EtOAc (3 mL). The organic solution was washed with 10% LiCl (3×2 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 3/1 hexane/EtOAc to afford title compound as a solid (0.001 g, 33%): MS (ESI+) 629 (M++H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07030118B2 |
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| Source dataset | uspto-grants-2006_04 |
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| ORD ID | ord-245f5d3e53854ad2bb7325dfccf16396 |
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| Source note | uspto-grants-2006_04 |
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