HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → tert-Butyl 4-({2-[4-(5-chloro-2-nitrophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Propylphosphonic anhydride | HCID 111923 | — |
| Reactant | Benzoic acid, 4-amino-, 1,1-dimethylethyl ester | HCID 233272 | — |
| Reactant | 2-[4-(5-Chloro-2-nitrophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]propanoic acid | HCID 117622839 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | tert-Butyl 4-({2-[4-(5-chloro-2-nitrophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoate | HCID 117622777 | — |
Reaction Steps
Under argon and at RT, 25 mg (0.13 mmol) of tert-butyl 4-aminobenzoate, 44 μl (0.26 mmol) of N,N-diisopropylethylamine and 74 μl (50% strength in DMF, 0.13 mmol) of T3P were added to a solution of 30 mg (0.09 mmol) of 2-[4-(5-chloro-2-nitrophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]propanoic acid (racemate) in 2 ml of DMF, and the mixture was stirred at RT for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 32 mg (71% of theory)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09434690B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-a2965565d5e1494a88ca9d214a0993c4 |
| Source note | uspto-grants-2016_09 |