HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 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 | Diisopropylethylamine | HCID 81531 | — |
| 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 | 145.5% |
Reaction Steps
The mixture of 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (300 mg), 3-[(methyloxy)carbonyl]benzoic acid (180 mg), HBTU (417 mg) and DIPEA (690 μL) in dichloromethane (DCM, 25 mL) was stirred at room temperature overnight. It was concentrated. Separation via CombiFlash (MeOH, DCM) then afforded the desired product (670 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08067408B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-f5d30a84dfe041de9c178c3bb1d580dc |
| Source note | uspto-grants-2011_11 |