Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | HCID 86762287 | HCID 86762287 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66751648 | HCID 66751648 | 69% |
Reaction Steps
Process 2: The dichloromethane (3 mL) solution of 2-{2-[4-butyl-5-[(2′-cyanobiphenyl-4-yl)methyl]-2-methyl-6-oxopyrimidin-1(6H)-yl]pyrimidin-5-yl oxy}acetic acid (51 mg, 0.1 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride salt (29 mg, 0.15 mmol) and 1-hydroxybenzotriazol-hydrate (21 mg, 0.15 mmol) was stirred at room temperature for 1 hr. Ammonia (28% aqueous solution, 0.5 mL) was added thereto and stirred at room temperature for 4 hrs. The reaction mixture was added water and extracted with chloroform. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residues were subjected to silica gel column chromatography (chloroform/methanol) to obtain 2-{2-{4-butyl-5-[(2′-cyanobiphenyl-4-yl)methyl]-2-methyl-6-oxopyrimidin-1(6H)-yl}pyrimidin-5-yl oxy}acetamide (35 mg, 69%) as a colorless and transparent oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08664226B2 |
|---|
| Source dataset | uspto-grants-2014_03 |
|---|
| ORD ID | ord-4351f1cdf7e94178aa01f4d33d641629 |
|---|
| Source note | uspto-grants-2014_03 |
|---|