HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-1-methyl-1H-1,2,4-triazole-3-carboxamide
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 | 1-methyl-1H-1,2,4-triazole-3-carboxylic acid | HCID 21981802 | — |
| Reactant | 6-(1H-indol-4-yl)-1H-indazol-4-amine | HCID 58268019 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-1-methyl-1H-1,2,4-triazole-3-carboxamide | HCID 44539958 | 51.4% |
Reaction Steps
HATU (248 mg) and DIPEA (0.211 ml) were added to a flask containing 1-methyl-1H-1,2,4-triazole-3-carboxylic acid (51 mg) in DMF (1 ml). The reaction was stirred for 30 min under nitrogen. 6-(1H-Indol-4-yl)-1H-indazol-4-amine (50 mg) was added and the mixture was stirred for 3 h at RT under nitrogen. The reaction mixture was applied to an aminopropyl SPE cartridge (5 g) and left for 3 h. The column was washed with 10% methanol in DCM. The appropriate fractions were combined and the solvent was evaporated. The residue was dissolved in methanol:DMSO (1 ml, 1:1) and purified by mass directed preparative HPLC (Method A) to give title compound (37 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08658635B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-569873561e0d48fd9d6fe49fca6c888c |
| Source note | uspto-grants-2014_02 |