HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → {1-[N'-(3-(2,2-Dimethyl-1-methylcarbamoyl-propylcarbamoyl)-3-hydroxy-4-phenyl-butyl]-N'-(4-pyridin-3-yl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}carbamic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-Pyridinylboronic acid | HCID 2734378 | — |
| Reactant | Tri-tert-butylphosphine tetrafluoroborate | HCID 2734635 | — |
| Reactant | (1-{N'-(4-Bromobenzyl)-N'-[3-(2,2-dimethyl-1-methylcarbamoyl-propylcarbamoyl)-3-hydroxy-4-phenyl-butyl]-hydrazinocarbonyl}2,2-dimethylpropyl)carbamic acid methyl ester | HCID 68677269 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | {1-[N'-(3-(2,2-Dimethyl-1-methylcarbamoyl-propylcarbamoyl)-3-hydroxy-4-phenyl-butyl]-N'-(4-pyridin-3-yl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}carbamic acid methyl ester | HCID 68678997 | 44% |
Reaction Steps
A mixture of compound (53) (69 mg, 0.10 mmol), 3-pyridylboronic acid (37 mg, 0.30 mmol), Pd(OAc)2 (1.1 mg, 0.0050 mmol), [(t-Bu)3PH]BF4 (3.0 mg, 0.010 mmol) and K2CO3 (41.5 mg, 0.30 mmol), H2O (0.30 mL) and 1,2-dimethoxyethane (1.0 mL) in a 2.0 mL microwave vial was irradiated to 80° C. for 20 min. The reaction mixture was filtered through celite and the solvent evaporated under reduced pressure. The residue was purified by preparative RP-LC-MS which gave 30.1 mg of the title compound (44% yield) as a colorless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07807677B2 |
| Source dataset | uspto-grants-2010_10 |
| ORD ID | ord-7985f5aee27a4790be518cda79701421 |
| Source note | uspto-grants-2010_10 |