HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 3-(4-methyl-imidazol-1-yl)-N-[3-(2-oxo-2,3-dihydro-1H-indol-6-ylamino)-phenyl]-5-trifluoromethyl-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid | HCID 46900241 | — |
| Reactant | 6-((3-Aminophenyl)amino)indolin-2-one | HCID 59397049 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-(4-methyl-imidazol-1-yl)-N-[3-(2-oxo-2,3-dihydro-1H-indol-6-ylamino)-phenyl]-5-trifluoromethyl-benzamide | HCID 59804309 | — |
Reaction Steps
To a solution of 6-(3-Amino-phenylamino)-1,3-dihydro-indol-2-one (36 mg, 0.15 mmol) and 3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoic acid (53 mg, 0.195 mmol) in DMF (1.5 mL) is added N,N-diisopropylethylamine (78 μL, 0.45 mmol) followed by addition of HATU (63 mg, 0.165 mmol). The mixture is stirred at ambient temperature overnight. The mixture is diluted with EtOAc and washed with 10% Na2S2O3 aqueous solution and brine. The organic layer is separated, dried over MgSO4, and concentrated. The crude product is used in the next step without further purification: LC-MS: 492.1 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08101608B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-175d29bce9554219b4a2cade2a350a2c |
| Source note | uspto-grants-2012_01 |