HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-N-(2-piperidin-3-ylethyl)-1,3-oxazole-4-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | Tert-butyl 3-(2-aminoethyl)piperidine-1-carboxylate | HCID 5001227 | — |
| Reactant | 2-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazole-4-carboxylic acid | HCID 58393098 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-N-(2-piperidin-3-ylethyl)-1,3-oxazole-4-carboxamide | HCID 46175908 | — |
| Product | Tert-butyl 3-[2-({[2-({cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazol-4-yl]carbonyl}amino)ethyl]piperidine-1-carboxylate | HCID 67328832 | — |
Reaction Steps
The title compound was prepared according to general procedure AH using 2-({cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazole-4-carboxylic acid (38 mg, 100 mop, EDCI (23 mg, 120 mop, HOBt monohydrate (18 mg, 120 μmol), DIPEA (69 μL, 400 mol), tert-butyl 3-(2-aminoethyl)piperidine-1-carboxylate (23 mg, 100 μmol) and DMF (750 L). The resulting crude compound was purified by FCC eluting with 100% EtOAc to afford tert-butyl 3-[2-({[2-({cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazol-4-yl]carbonyl}amino)ethyl]piperidine-1-carboxylate. Yield: 38 mg, 64%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08623859B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-c7eeac8c0c384b4f8cfbf505a0051400 |
| Source note | uspto-grants-2014_01 |