HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylcarbodiimide → 2-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4-methoxy-N-(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)butanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylcarbodiimide | HCID 12734 | — |
| Reactant | 5-amino-2H-1,3-benzodiazol-2-one | HCID 15250547 | — |
| Reactant | 2-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4-methoxybutanoic acid | HCID 117622944 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4-methoxy-N-(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)butanamide | HCID 117622956 | — |
Reaction Steps
70 mg (186 μmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4-methoxybutanoic acid (racemate), 27.7 mg (186 μmol, 1.0 eq.) of 5-aminobenzimidazolone, 26.4 mg (186 μmol) of Oxima and 28.9 μl (186 μmol) of DIC in 3.9 ml of dimethylformamide were reacted according to General Method 5. The crude product was purified by preparative HPLC (column: Chromatorex 125 mm×30 mm, 10 μm, mobile phase: water/0.1% formic acid and acetonitrile/0.1% formic acid, gradient 10% acetonitrile to 90% acetonitrile) and then subjected to basic extraction (aqueous sodium hydroxide solution/ethyl acetate). Yield: 44 mg (47% of theory)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09434690B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-b5f01503dc334bb1aa5fa871c713b8dc |
| Source note | uspto-grants-2016_09 |