HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-(1-hydroxyethyl)-4-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-isochromen-1-one → 3-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-isochromen-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-(1-hydroxyethyl)-4-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-isochromen-1-one | HCID 118131364 | — |
| Reactant | 3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(5-(piperazin-1-ylmethyl)thiophen-2-yl)-1H-isochromen-1-one dihydrochloride | HCID 118131492 | — |
| Reactant | HCID 178492931 | HCID 178492931 | — |
| Product | 3-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-isochromen-1-one | HCID 118131507 | 62.8% |
Reaction Steps
The title compound was made in a similar way as that of the compound of example 134, step a, from 3-(1-hydroxyethyl)-4-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-isochromen-1-one (Intermediate B39, 411 mg, 1.069 mmol), and 3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (intermediate G1, 305 mg, 1.176 mmol) to give 3-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-isochromen-1-one (420 mg, 0.671 mmol, 62.8% yield) as a brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321776B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-c9fcae36fec14c7ebceef62fc4e8d688 |
| Source note | uspto-grants-2016_04 |