Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isovaleric Acid | HCID 10430 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Calcium Chloride | HCID 5284359 | — |
| 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 | 5-Bromo-N1-methylbenzene-1,2-diamine | HCID 12198270 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 21504713 | HCID 21504713 | — |
Reaction Steps
To a solution of 5-bromo-N1-methylbenzene-1,2-diamine (159 mg), isovaleric acid (0.087 ml) and N,N-diisopropylethylamine (0.41 ml) in DMF (2 ml) was added HATU (316 mg) at room temperature. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 3 h. After evaporation of the mixture, the residue was purified by NH silica gel column chromatography (hexane/EtOAc). The resulting residue was stirred in AcOH (2.0 ml) at 80° C. for 1 h. After evaporation, the residue was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (156 mg) as a pale yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09365540B2 |
|---|
| Source dataset | uspto-grants-2016_06 |
|---|
| ORD ID | ord-eabc449f317f4e259a4b46258dc29b2c |
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| Source note | uspto-grants-2016_06 |
|---|
