HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → N-(7,7-Dimethyl-6-oxo-5-pentyl-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-2-trifluoromethoxy-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 2-(Trifluoromethoxy)benzoic acid | HCID 2777223 | — |
| Reactant | 2-Amino-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one | HCID 59300824 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-(7,7-Dimethyl-6-oxo-5-pentyl-1,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-2-trifluoromethoxy-benzamide | HCID 59300870 | 52.3% |
Reaction Steps
To a solution of D5 (849 mg), TBTU (987 mg; 3.07 mmol) and DIPEA (1 ml) in THF (25 ml) is added drop-wise a solution of 2-trifluoromethoxy-benzoic acid (737 mg; 3.58 mmol) in THF (5 ml) at 0° C. over a period of 15 min. The reaction mixture is warmed to RT and stirred for 20 h. After completion of the reaction the solution is filtered over Alox B and concentrated in vacuo. Purification by flash chromatography on silica gel eluting with cyclohexane/EtOAc yield the desired compound (736 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07714010B2 |
| Source dataset | uspto-grants-2010_05 |
| ORD ID | ord-310927259a32447fbb0c7b502f477e2e |
| Source note | uspto-grants-2010_05 |