Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 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 | N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide | HCID 10214710 | — |
| Reactant | HCID 57722436 | HCID 57722436 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 10053338 | HCID 10053338 | 57% |
Reaction Steps
The above carboxylic acid (100 mg, 0.335 mmol) and N-(3-amino-5-tert-butyl-2-methoxyphenyl)-methanesulfonamide (91 mg, 0.335 mmol) were dissolved in 2 mL DMF and stirred at room temperature. After about 10 min, HATU (127 mg, 0.335 mmol) and HOBt (45 mg, 0.335 mmol) were added followed by diisopropylamine (87 mg, 0.670 mmol, 120 uL) and the solution was stirred at room temperature. After stirring for eight days, the entire reaction was partitioned between EtOAc (75 mL) and water (50 mL). The layers were separated and the organic portion was washed with water (2×25 mL), brine (25 mL), dried (MgSO4), filtered and the solvent was removed to afford a tan solid. Column chromatography (EtOAc, silica gel) afforded the title compound as a colorless solid (105 mg, 57%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07550461B2 |
|---|
| Source dataset | uspto-grants-2009_06 |
|---|
| ORD ID | ord-713cfe73ac9d423b841b689ca83d1cc7 |
|---|
| Source note | uspto-grants-2009_06 |
|---|
