HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → HCID 10053957, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Indole-2-carboxylic acid | HCID 72899 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HOAt | HCID 181649 | — |
| 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 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 10053957 | HCID 10053957 | — |
Reaction Steps
To a solution of the indole carboxylic acid (360 mg, 0.93 mmol) in 4 mL of DMF was added Hunig's base (418 uL, 2.4 mmol). After 5 min, HATU (439 mg, 1.12 mmol) and HOAt (12 mg, 0.09 mmol) were added and then N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide (253 mg, 0.93 mmol). The mixture was stirred overnight. The reaction mixture was diluted with EtOAc, washed with water, brine, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (1:2 hexanes-EtOAc) to give 390 mg of the desired amide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07078419B2 |
| Source dataset | uspto-grants-2006_07 |
| ORD ID | ord-65517cb8e3c04b42a5dcdb707311818a |
| Source note | uspto-grants-2006_07 |