Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 5-(2,4-Difluorophenoxy)-1-isobutyl-1H-indazole-6-carboxylic acid | HCID 57418763 | — |
| Reactant | HCID 67413405 | HCID 67413405 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,1-Dichloroethane | HCID 6365 | — |
| Product | HCID 67413214 | HCID 67413214 | 89% |
Reaction Steps
5-(2,4-Difluorophenoxy)-1-isobutyl-1H-indazole-6-carboxylic acid (17d; prepared according to Example 110) (0.022 g, 0.064 mmol) was stirred with HOBt (0.011 g, 0.070 mmol) and EDCI (0.014 g, 0.070 mmol) in dichloroethane (1 mL) for 10 minutes at room temperature. To this mixture was then added a suspension of (S)-methyl 4-((4-methoxybenzyl)(isopropyl)amino)-2-(tert-butoxycarbonyl)butanoate hydrochloride (0.025 g, 0.067 mmol) and triethylamine (0.054 mL, 0.384 mmol) in dichloromethane (2 mL). The mixture was stirred at room temperature for 16 hours. The solution was filtered through Celite and concentrated under reduced pressure. The crude oil was chromatographed eluting with 2% MeOH in dichloromethane with 1% triethylamine to provide 0.035 g of viscous pale yellow oil (89% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08518983B2 |
|---|
| Source dataset | uspto-grants-2013_08 |
|---|
| ORD ID | ord-ca32863e00374364bcb0445515a67393 |
|---|
| Source note | uspto-grants-2013_08 |
|---|