HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → N-{[3-(4-{[4-[5-Fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)phenyl]carbonyl}-N-methyl-L-alanine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | N-Methyl-L-Alanine | HCID 5288725 | — |
| 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 | 3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)benzoic acid | HCID 25180783 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-{[3-(4-{[4-[5-Fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)phenyl]carbonyl}-N-methyl-L-alanine | HCID 57672635 | 37.1% |
Reaction Steps
N,N-Diisopropylethylamine (0.149 mL, 0.855 mmol) and HATU (68.3 mg, 0.18 mmol) were added to a solution of 3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)benzoic acid (96 mg, 0.171 mmol) in DMF (1 mL) and the solution stirred at room temperature under nitrogen for 10 min. N-methyl-L-alanine (44.1 mg, 0.43 mmol) was added and the mixture stirred at room temperature for 5 days. The resulting suspension was diluted with methanol and DMSO to give a solution which was filtered and purified by mass directed autopreparation (System B) to give the title compound (40.9 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178573B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-839a147f64304f1e95e5462a0cde9efd |
| Source note | uspto-grants-2012_05 |