HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 9-(1-Methyl-1H-imidazol-2-yl)-8(4-(pyrrolidin-1-ylmethyl)phenyl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | 4-(9-(1-methyl-1H-imidazol-2-yl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)benzaldehyde | HCID 136368567 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 9-(1-Methyl-1H-imidazol-2-yl)-8(4-(pyrrolidin-1-ylmethyl)phenyl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one | HCID 136186320 | 22.4% |
Reaction Steps
A mixture of 4-(9-(1-methyl-1H-imidazol-2-yl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)benzaldehyde (80 mg, 0.22 mmol), acetic acid (60 uL) and pyrrolidine (1.05 g, 15 mmol) in acetonitrile (7 mL) was stirred at room temperature for 4 hr. To this mixture was added NaCNBH3 (36 mg, 0.67 mmol) at 0° C. After the addition, the mixture was stirred at room temperature for 4 hr. Upon removal of solvents under reduced pressure, the residue was washed with ethyl acetate and filtered. The filtrate was concentrated to give the title compound as a white solid (21 mg, yield 22%). LC-MS (ESI) m/z: 427 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08999987B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-5df480fc45c14d8eb17e992527b59d2f |
| Source note | uspto-grants-2015_04 |