HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → methyl 3-cyclohexyl-1-methyl-2-{2-[2-(methyl {2-[2-(methylamino)ethoxy]ethyl}amino)-2-oxoethoxy]phenyl}-1H-indole-6-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,5-Bis(methylamino)-3-oxapentane | HCID 2724770 | — |
| 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 | {2-[3-cyclohexyl-6-(methoxycarbonyl)-1-methyl-1H-indol-2-yl]phenoxy}acetic acid | HCID 58317804 | — |
| Product | methyl 3-cyclohexyl-1-methyl-2-{2-[2-(methyl {2-[2-(methylamino)ethoxy]ethyl}amino)-2-oxoethoxy]phenyl}-1H-indole-6-carboxylate | HCID 67226641 | 91% |
Reaction Steps
A solution of intermediate 5 (650 mg, 1.54 mmol), N-methyl-2-(methylaminoethyloxy)ethylamine (1.02 g, 7.71 mmol), diisopropylethylamine (808 μL, 4.63 mmol) and HATU (880 mg, 2.31 mmol) in dry THF (25 mL) was stirred at room temperature overnight. Then, the reaction mixture was concentrated under vacuum. The residue was partitioned between AcOEt and water. The organic layer was dried over anhydrous Na2SO4 and evaporated to yield 750 mg (91%) of methyl 3-cyclohexyl-1-methyl-2-{2-[2-(methyl {2-[2-(methylamino)ethoxy]ethyl}amino)-2-oxoethoxy]phenyl}-1H-indole-6-carboxylate 6: m/z=536 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08357687B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-2c2354355fb646f085656da99cee0b0c |
| Source note | uspto-grants-2013_01 |