HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tyramine → 3-[(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tyramine | HCID 5610 | — |
| Reactant | 3-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 86603269 | — |
| Product | 3-[(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 67044832 | — |
Reaction Steps
Intermediate 36 was coupled with tyramine following procedure F. The resulting product was deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 468. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.2 (d, 2H), 8.0 (d, 1H) 7.6 (d, 1H) 7.5 (t, 1H), 7.2 (d, 1H), 7.1 (d, 2H), 6.7 (d, 2H), δ 4.6 (s, 2H), 3.5-3.4 (m, 6H), δ 3.2-3.1 (m, 1H), 3.0 (s, 3H), δ 2.9 (t, 2H), δ 2.2-2.0 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08268822B2 |
| Source dataset | uspto-grants-2012_09 |
| ORD ID | ord-aef589a747c54295a761780e159e7ce6 |
| Source note | uspto-grants-2012_09 |