HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → 3-(Aminomethyl)-N-(4-chlorobenzyl)-2-{[[(2R)-2-hydroxy-2-pyridin-2-ylethyl](methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 3-(azidomethyl)-N-(4-chlorobenzyl)-2-{[[(2R)-2-hydroxy-2-pyridin-2-ylethyl](methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide | HCID 59985226 | — |
| Catalyst | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Water | HCID 962 | — |
| Product | 3-(Aminomethyl)-N-(4-chlorobenzyl)-2-{[[(2R)-2-hydroxy-2-pyridin-2-ylethyl](methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide | HCID 59985219 | 78.6% |
Reaction Steps
A solution of 111 mg of 3-(azidomethyl)-N-(4-chlorobenzyl)-2-{[[(2R)-2-hydroxy-2-pyridin-2-ylethyl](methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide and 58 mg of triphenylphosphine in 2 mL of THF containing 5 drops of water is stirred overnight, then concentrated under reduced pressure with CHCl3/MeOH azeotrope. Flash chromatography on silica gel using 4-10% methanolic ammonia in CH2Cl2 provides 83.1 mg of the amine as a white solid. Recrystallization from acetonitrile furnishes white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06852731B2 |
| Source dataset | uspto-grants-2005_02 |
| ORD ID | ord-784bab6bb17742e8a9275d0917dbc3cb |
| Source note | uspto-grants-2005_02 |