HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium triacetoxyborohydride → N-(5-butyl-2-pyridinylmethyl)-N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 5-n-Butylpyridine-2-carboxaldehyde | HCID 21396266 | — |
| Reactant | N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine | HCID 21985008 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-(5-butyl-2-pyridinylmethyl)-N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine | HCID 22018809 | — |
Reaction Steps
Using general procedure B: N-(1H-benzimidazol-2-ylmethyl)-N-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.1258 g, 0.316 mmol) and 5-n-butylpyridine-2-carboxaldehyde (0.0603 g, 0.294 mmol) were reacted with NaBH(OAc)3 (0.0942 g, 0.444 mmol) in CH2Cl2 (2.5 mL). Purification of the crude material by radial chromatography (2 mm TLC plate, 50:1:1 CH2Cl2: CH3OH: NH4OH) provided 0.0713 g (45%) of AMD9398 (free base).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07084155B2 |
| Source dataset | uspto-grants-2006_08 |
| ORD ID | ord-b8796c8cf3334b43b0cdd5ad9d83bed5 |
| Source note | uspto-grants-2006_08 |