HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 4-Methyl-2-(2-(4-(3-(piperidin-1-yl)propoxy)phenyl)acetamido)thiophene-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 2-Amino-4-methylthiophene-3-carboxamide | HCID 293810 | — |
| Reactant | 2-(4-(3-(Piperidin-1-yl)propoxy)phenyl)acetic acid | HCID 44769635 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | dichloromethane N,N-dimethylformamide | HCID 22350042 | — |
| Product | 4-Methyl-2-(2-(4-(3-(piperidin-1-yl)propoxy)phenyl)acetamido)thiophene-3-carboxamide | HCID 59636676 | — |
Reaction Steps
To a stirring mixture of 2-(4-(3-(piperidin-1-yl)propoxy)phenyl)acetic acid (800 mg) in DMF/DCM (6 mL, 1:1) was added triethylamine (1.2 mL), DMAP (180 mg), 2-amino-4-methylthiophene-3-carboxamide (440 mg), and EDCI (1.1 g). The reaction mixture was stirred at rt overnight, quenched with saturated NaHCO3 solution and extracted with EtOAc. The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified via preparative HPLC to give 4-methyl-2-(2-(4-(3-(piperidin-1-yl)propoxy)phenyl)acetamido)thiophene-3-carboxamide. Method[7], MS (ESI) 416.2 [M+H], Retention time=2.254 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08450363B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-46e8287aa9284f33b96d6a694ee4c651 |
| Source note | uspto-grants-2013_05 |