HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-(Methoxycarbonyl)benzoic acid → 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 | 3-(Methoxycarbonyl)benzoic acid | HCID 601880 | — |
| 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 | 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 | 109.9% |
Reaction Steps
A mixture of 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (2.0 g, 0.0059 mol) in DCM (60 mL) with 3-[(methyloxy)carbonyl]benzoic acid (1.16 g, 0.00648 mol) and HATU (2.68 g, 0.00706 mol) and TEA (1.19 g, 1.64 mL, 0.0118 mol) gave a yellow solution upon stirring overnight at RT. The solution was washed in turn with sat. aq. NaHCO3, H2O, and sat. aq. NaCl, then dried (Na2SO4), and concentrated to a viscous syrup/foam (3.68 g). This was purified on a ‘CombiFlash’ 40 g silica gel column (hexane-EtOAc) [20-100% EtOAc] to afford the title compound (3.02 g). LC-MS m/z 466.1 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08067408B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-83771cc58eae484eba6e044e2501db0b |
| Source note | uspto-grants-2011_11 |