Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 1-[3-(4-Methylpiperazin-1-yl)phenyl]methanamine | HCID 4961252 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | 6-Bromo-4-chlorophthalazin-1(2H)-one | HCID 53308487 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 24946341 | HCID 24946341 | — |
Reaction Steps
A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.58 mmol), 3-(4-methyl-piperazin-1-yl)-benzylamine (111 mg, 0.64 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (132 mg, 0.17 mmol) and NaOt-Bu (140 mg, 1.45 mmol) in DMA (6 mL) was heated at 80° C. for 1 h. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with water (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded the title compound. 4-Chloro-6-[3-(4-methyl-piperazin-1-yl)-benzylamino]-2H-phthalazin-1-one: 50 mg (22.5%): m/z (M+H)=384. 1H-NMR (DMSO-d6) δ: 12.33 (s, 1H), 7.91 (d, 1H), 7.59 (m, 1H), 7.16 (m, 2H), 6.98 (s, 1H), 6.80 (m, 3H), 4.34 (d, 2H), 3.11 (m, 4H), 2.42 (m, 4H), 2.20 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08044041B2 |
|---|
| Source dataset | uspto-grants-2011_10 |
|---|
| ORD ID | ord-f18cf24c00984414862672f7d3615762 |
|---|
| Source note | uspto-grants-2011_10 |
|---|
