HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-(Methoxycarbonyl)benzoic acid | HCID 601880 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 5-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine | HCID 59683214 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoate | HCID 57813262 | 62.3% |
Reaction Steps
To a solution of 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-amine (0.303 g, 1.0 mmol) in CH2Cl2 (10 mL) was added 3-[(methyloxy)carbonyl]benzoic acid (0.198 g, 1.1 mmol), HBTU (0.569 g, 1.5 mmol), and Et3N (0.281 mL, 2.0 mmol). The mixture was stirred at room temperature for 22 h. The reaction was quenched with H2O (1 mL). The organic layer was separated, directly load onto silica gel cartridge and purified by CombiFlash chromatograph to afford the title compound 0.29 g (55%). LC-MS m/z 466 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08067408B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-61f53ac38b524f5ba3001c8b31749cb7 |
| Source note | uspto-grants-2011_11 |