HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetone → 5-Cyano-1-[3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)indol-5-yl]-1H-benzimidazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | 2-(Ethoxymethylene)propanedinitrile | HCID 67152 | — |
| Reactant | 5-(4-Cyano-2-nitrophenyl)amino-3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-1H-indole | HCID 53865648 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-Cyano-1-[3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)indol-5-yl]-1H-benzimidazole | HCID 54238357 | 10% |
Reaction Steps
5-(4-Cyano-2-nitrophenyl)amino-3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-1H-indole was used. Reduction was by aqueous FeSO4 in ethanol, the cyclization reaction used ethoxymethylene malononitrile, and the cyclization reaction was heated for 56 hours. Chromatography using 5% acetone in methylene chloride afforded the title compound (10%) as a brown foam: Rf =0.5 in 5% acetone in methylene chloride; HRMS calculated for C26H25N5O2 439.2011, found 439.1999.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05886008 |
| Source dataset | uspto-grants-1999_03 |
| ORD ID | ord-f37f864d6e5d4083845d628c313d5b37 |
| Source note | uspto-grants-1999_03 |