HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 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 | Dimethylformamide | HCID 6228 | — |
| 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-piperazin-1-yl)-5-trifluoromethyl-benzoic acid hydrochloride | HCID 46738289 | — |
| Reactant | 6-(3-Amino-phenoxy)-1,3-dihydro-indol-2-one | HCID 59804318 | — |
| 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-phenoxy)-1,3-dihydro-indol-2-one (200 mg, 0.83 mmol) and 3-(4-methyl-piperazin-1-yl)-5-trifluoromethyl-benzoic acid hydrochloride (291 mg, 0.89 mmol) in DMF (10 mL) is added N,N-diisopropylethylamine (164 μL, 1 mmol) followed by addition of HATU (380 mg, 1 mmol). The mixture is stirred at ambient temperature overnight. The mixture is diluted with EtOAc and washed with 10% aq Na2S2O3 solution and brine. The organic layer is separated, dried over MgSO4, and concentrated. The crude (310 mg) was used in the next step without further purification. LC/MS: 511.2 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08101608B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-9145b9933c9048a0b6eb2985d70b8338 |
| Source note | uspto-grants-2012_01 |