HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclopropanemethanamine → N-tert-Butyl-3-((4-(5-chloro-4-(3-(cyclopropylmethyl)ureido)-2-ethoxybenzoyl)piperazin-1-yl)methyl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclopropanemethanamine | HCID 75646 | — |
| Reactant | 4-Nitrophenyl chloroformate | HCID 82129 | — |
| Reactant | 3-((4-(4-Amino-5-chloro-2-ethoxybenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide | HCID 57917664 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-tert-Butyl-3-((4-(5-chloro-4-(3-(cyclopropylmethyl)ureido)-2-ethoxybenzoyl)piperazin-1-yl)methyl)benzamide | HCID 57917638 | 3% |
Reaction Steps
3-((4-(4-Amino-5-chloro-2-ethoxybenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (250 mg, 0.525 mmol) and 4-nitrophenol chloroformate (425.7 mg, 0.525 mmol) were combined and stirred in dichloromethane for 1 hour. Cyclopropylmethylamine (0.114 g, 1.6 mmol, 0.139 mL) was added and the reaction was stirred for 30 minutes. The reaction mixture was diluted with water and flushed through a hydrophobic frit. The organic phase was concentrated under reduced pressure and purified by basic reverse phase HPLC to give the title compound (9.1 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08314091B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-faa34a2ff33c4c1b8f6816f6b7ee09ab |
| Source note | uspto-grants-2012_11 |