HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tyramine → 4-[2-(4-{3-[3(S)-(1H-Indol-3-ylmethyl)-piperazin-1-ylmethyl]-phenyl}-pyrimidin-2-ylamino)-ethyl]-phenol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tyramine | HCID 5610 | — |
| Reactant | 4-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-2-(1H-indol-3-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester | HCID 86603303 | — |
| Product | 4-[2-(4-{3-[3(S)-(1H-Indol-3-ylmethyl)-piperazin-1-ylmethyl]-phenyl}-pyrimidin-2-ylamino)-ethyl]-phenol | HCID 58603773 | — |
Reaction Steps
Intermediate 109 was coupled with tyramine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 520. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.51 (s, 1H), 8.29 (d, 2H), 7.81 (d, 1H), 7.55 (m, 3H), 7.34 (d, 1H), 7.25 (s, 1H), 7.02 (m, 4H), 6.69 (s, 2H), 4.54 (m, 2H), 4.08 (m, 1H), 3.90 (m, 2H), 3.61 (m, 4H), 3.25 (m, 4H), 2.92 (t, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07732444B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-b86592ad3523402ab03c6d0328b0ca81 |
| Source note | uspto-grants-2010_06 |