HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → bis(4-methylpiperazin-1-yl)methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1-Methylpiperazine | HCID 53167 | — |
| 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 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | bis(4-methylpiperazin-1-yl)methanone | HCID 515613 | 19% |
Reaction Steps
In THF (20 mL) were dissolved 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amine)pyrimidine-5-carboxylic acid (153 mg, 0.41 mmol), 1-methylpiperazine (49 mg, 0.49 mmol) and HATU (188 mg, 0.49 mmol). The solution was cooled in an ice bath then DIEA was added dropwisely (0.14 mL, 0.82 mmol). The reaction was conducted at ambient temperature for 8 h, followed by addition of water (20 mL) and extraction with ethyl acetate or DCM. The organic phase was dried, concentrated and purified by silica gel column chromatography (DCM/methanol=25/1) to give 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)pyrimidin-5-yl)(4-methylpiperazin-1-yl)ketone (35 mg, 19% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359371B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-22093cadf69e4511962a08139cb6ef57 |
| Source note | uspto-grants-2016_06 |