Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamine | HCID 13822957 | — |
| Reactant | 4-[[(1R)-3-(4-Morpholinyl)-1-[(phenylthio)methyl]propyl]amino]-3-[(trifluoromethyl)sulfonyl]benzenesulfonamide | HCID 25058454 | — |
| Reactant | HCID 67980981 | HCID 67980981 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 67980849 | HCID 67980849 | 44.3% |
Reaction Steps
3-Bromo-4,5,7,8-tetrahydro-1,2,3a,6-tetraaza-azulene-6-carboxylic acid tert-butyl ester (154 mg, 0.486 mmol), 4-((R)-3-morpholin-4-yl-1-phenylsulfanylmethyl-propylamino)-3-trifluoromethane sulfonyl-benzenesulfonamide (269 mg, 0.486 mmol), (1S,2S)—N,N′-dimethyl-cyclohexane-1,2-diamine (0.011 mL, 0.146 mmol), cesium carbonate (269 mg, 0.825 mmol), and copper (I) iodide (13.87 mg, 0.073 mmol) were added to a microwave vial followed by toluene (8 mL). The reaction mixture was degassed for 15 minutes under nitrogen, sealed, and then heated conventionally to 90° C. for 14 hours. The crude material was directly purified via flash chromatography on silica gel (0-15% 2N NH3 in methanol in CH2Cl2) to afford the title compound (170 mg, 44% yield). MS [m/z; (M+1)+]: 790.5
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08809352B2 |
|---|
| Source dataset | uspto-grants-2014_08 |
|---|
| ORD ID | ord-5cbc3d8d676d402a94ab9908c270c48a |
|---|
| Source note | uspto-grants-2014_08 |
|---|
