HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium triacetoxyborohydride → Methyl 2-(4-((3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propylamino)methyl)phenyl)acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | Methyl 2-(4-formylphenyl)acetate | HCID 19363032 | — |
| Reactant | 1-(3-aminopropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine | HCID 22344428 | — |
| Catalyst | Acetic Acid | HCID 176 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 2-(4-((3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propylamino)methyl)phenyl)acetate | HCID 68430910 | 37.9% |
Reaction Steps
To the product from step (iv) (1.25 g) in THF (100 mL), methyl 2-(4-formylphenyl)acetate (0.818 g) was addded followed by sodium triacetoxyborohydride (0.885 g) and acetic acid (3 drops) and stirred at rt for 16 h. The reaction was quenched with water, extracted with DCM washed with sat. NaHCO3 (200 mL), dried and solvent removed. The resulting residue was dissolved in methanol and purified on SCX to give the subtitle compound (0.73 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08436178B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-37498085930444ceb970faed04e5b705 |
| Source note | uspto-grants-2013_05 |