HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 59784370, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 4-[2-(4-Methylpiperazin-1-yl)ethyl]aniline | HCID 24255480 | — |
| Reactant | Sodium 2-amino-3-nitrobenzoate | HCID 59785142 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59784370 | HCID 59784370 | 78.2% |
Reaction Steps
To a mixture of 2-amino-3-nitro-benzoic acid sodium salt (205 mg, 1.0 mmol), 4-[2-(4-methyl-piperazin-1-yl)-ethyl]-phenylamine (219 mg, 1.0 mmol) and HATU (400 mg, 1.05 mmol) in DMF (2 mL) was added DIEA (0.52 mL, 388 mg, 3.0 mmol). The reaction mixture was stirred at room temperature for 1 h and heated at 70° C. for 1 h, and then evaporated under reduced pressure. The residue was purified by chromatography (50:10:1 CH2Cl2/MeOH/28% aqueous NH4OH) to afford the title compound (300 mg, 78%). 1H NMR (MeOH-d4) δ 2.44 (s, 3H), 2.50-2.85 (12H), 6.74 (dd, J=9 Hz and 9 Hz, 1H), 7.23 (d, J=9 Hz, 2H), 7.58 (d, J=9 Hz, 2H), 7.91 (d, J=9 Hz, 1H), 8.29 (d, J=9 Hz, 1H). ESI-MS m/z 384.5 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08629147B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-2c59aadaa8ae48b1b955b40c53d4d96a |
| Source note | uspto-grants-2014_01 |