HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,1'-Carbonyldiimidazole → 1h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)-n-[2-[(phenylmethyl)amino]ethyl]-
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | N-Benzylethylenediamine | HCID 77801 | — |
| Reactant | 1h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)- | HCID 57418739 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)-n-[2-[(phenylmethyl)amino]ethyl]- | HCID 42611124 | 100% |
Reaction Steps
A solution of 5-(4-fluorophenoxy)-1-isobutyl-1H-indazole-6-carboxylic acid (compound 10g, prepared as described in Example 46) in THF was treated with carbonyldiimidazole (1.2 equivalents) at room temperature under nitrogen atmosphere. After stirring at for 18 hours, the reaction was treated with N1-benzyl-ethane-1,2-diamine (1 equivalent). After an additional 18 hours, the solvent was allowed to slowly evaporate and the residue was purified in a Sep Pak cartridge eluting with a gradient of 100% CH2Cl2 to MeOH/CH2Cl2 to provide compound 11g-5 as an oil in 100% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07135575B2 |
| Source dataset | uspto-grants-2006_11 |
| ORD ID | ord-3cbf0c54e4104df6a1bca75c6101b530 |
| Source note | uspto-grants-2006_11 |