HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Pyrrolidineethanamine → 4-(2-{[4-ethylphenyl]amino-1-methylbenzimidazol-5-yloxy)(2-pyridyl)]-N-(2-pyrrolidinylethyl)carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Pyrrolidineethanamine | HCID 1344 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 4-(2-{[4-Ethylpheyl]amino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid | HCID 22040464 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-(2-{[4-ethylphenyl]amino-1-methylbenzimidazol-5-yloxy)(2-pyridyl)]-N-(2-pyrrolidinylethyl)carboxamide | HCID 131725838 | — |
Reaction Steps
To 4-(2-{[4-ethylpheyl]amino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid (1 eq) in tetrahydrofuran was added 2-pyrrolidinylethylamine (2 eq), HBTU (2 eq) and N,N-diisopropylethylamine (4 eq) and stir at ambient temperature for 16 h. The mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was concentrated and preparative chromatography yielded [4-(2-{[4-ethylphenyl]amino-1-methylbenzimidazol-5-yloxy)(2-pyridyl)]-N-(2-pyrrolidinyl-ethyl)carboxamide MS: MH+=484.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07071216B2 |
| Source dataset | uspto-grants-2006_07 |
| ORD ID | ord-6fb29f1c20dc42d685c70611cd0567a6 |
| Source note | uspto-grants-2006_07 |