HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → Trifluoroacetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Fluoro-2-nitrobenzene | HCID 73895 | — |
| Reactant | 1-Fluoro-3-methoxy-2-nitrobenzene | HCID 2782776 | — |
| Reactant | 3-Hydroxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzoic acid methyl ester | HCID 59814678 | — |
| Product | Trifluoroacetic acid | HCID 6422 | — |
| Product | 3-Methoxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzonitrile | HCID 59814741 | — |
Reaction Steps
Using an adaptation of Procedure 2, substituting 8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamine for the TFA salt of 3-hydroxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzoic acid methyl ester, 1a, 1-fluoro-3-methoxy-2-nitrobenzene, 1e for 2-fluoronitrobenzene, and cesium carbonate for potassium carbonate, the title compound 3-methoxy-4-(8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylamino)-benzonitrile, 1p was obtained as TFA salt and as a mixture of endo and exo isomers after purification via reverse phase HPLC (eluent gradient: 20% to 45% CH3CN in water containing 0.1% TFA). MS m/z=272 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07652005B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-5a32da4b4647401eafd9711c591fd798 |
| Source note | uspto-grants-2010_01 |