Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Pyridineethanamine | HCID 83275 | — |
| Reactant | Propylphosphonic anhydride | HCID 111923 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 69591877 | HCID 69591877 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 69591893 | HCID 69591893 | 102.5% |
Reaction Steps
A solution of 4-(2-aminoethyl)pyridine (0.017 g, 0.14 mmol) in 0.3 mL methylene chloride was added to 3-{4-[[3-(tetrahydro-pyran-2-yloxy)-benzyl]-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-acrylic acid (0.050 g, 0.09 mmol). Triethylamine (0.07 mL, 0.50 mmol), 1-propanephosphonic acid cyclic anhydride (0.06 mL of a 50 wt. % solution in ethyl acetate, 0.20 mmol), and catalytic DMAP were added. The reaction mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium bicarbonate was added and the aqueous solution was washed with methylene chloride. The organic layer was separated, PS-trisamine resin (0.050 g) was added, and the mixture was stirred at room temperature for three days. The resin was filtered off and the filtrate was concentrated to afford 0.059 g of the title compound of Step A. MS 640.4 (M+1)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07053212B2 |
|---|
| Source dataset | uspto-grants-2006_05 |
|---|
| ORD ID | ord-52eea1d1ed12422795fa7a25aff42349 |
|---|
| Source note | uspto-grants-2006_05 |
|---|