HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 3-(Isopropyl-{3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoyl}-amino)-propionic acid methyl ester trifluoroacetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | Methyl 3-[(propan-2-yl)amino]propanoate | HCID 12774812 | — |
| Reactant | 3-Methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoic acid trifluoroacetate | HCID 69949694 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-(Isopropyl-{3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoyl}-amino)-propionic acid methyl ester trifluoroacetate | HCID 69947487 | 93.3% |
Reaction Steps
To a stirred solution of 3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoic acid trifluoroacetate (0.025 g) and TBTU (0.021 g) in DMF (1 ml) was added DIPEA (0.022 ml) followed by 3-isopropylamino-propionic acid methyl ester (0.01 g) after 3 min. The reaction was stirred at room temperature for 18 h, and then concentrated under reduced pressure. The residue was subjected to preparative hplc to give the title compound (0.031 g) as a colourless oil, by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile and concentration under reduced pressure.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06326386B1 |
| Source dataset | uspto-grants-2001_12 |
| ORD ID | ord-e07a5ad8f0fe446187b3d6f39ccc3a9d |
| Source note | uspto-grants-2001_12 |