HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-Amino-3-phenylisoxazole → tert-butyl (1S,2R)-2-(4-cyano-3-(3-phenylisoxazol-5-ylamino)phenylamino)cyclohexylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-Amino-3-phenylisoxazole | HCID 261201 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Sodium Phenoxide Trihydrate | HCID 23681143 | — |
| Reactant | tert-butyl (1S,2R)-2-(3-bromo-4-cyanophenylamino)cyclohexylcarbamate | HCID 69283621 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | tert-butyl (1S,2R)-2-(4-cyano-3-(3-phenylisoxazol-5-ylamino)phenylamino)cyclohexylcarbamate | HCID 69284832 | 21.1% |
Reaction Steps
A mixture of tert-butyl (1S,2R)-2-(3-bromo-4-cyanophenylamino)cyclohexylcarbamate (150 mg, 0.380 mmol), 5-amino-3-phenylisoxazole (130 mg, 0.812 mmol), sodium phenoxide trihydrate (100 mg, 0.588 mmol), xantphos (30 mg, 0.051 mmol) and Pd2(dba)3 (30 mg, 0.032 mmol) in dioxane (2 mL) was degassed with Ar, then was heated at 170 C for 30 min by microwave. It was concentrated in vacuo. The residue was purified by HPLC to give tert-butyl (1S,2R)-2-(4-cyano-3-(3-phenylisoxazol-5-ylamino)phenylamino)cyclohexylcarbamate (38 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359375B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-e6bc3e69579441458410b6be05198da2 |
| Source note | uspto-grants-2016_06 |