HuagongsheHuagongshe Chemistry Print Report · For research reference only
Formaldehyde → (R)-N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-((3-(hydroxymethyl)-4-methylpiperazin-1-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | (R)-N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-((3-(hydroxymethyl)piperazin-1-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide | HCID 24994903 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (R)-N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-((3-(hydroxymethyl)-4-methylpiperazin-1-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide | HCID 57551779 | 85.2% |
Reaction Steps
The product of Example 85 (80 mg) was dissolved in dichloromethane (10 mL). Formaldehyde (0.057 mL) and sodium triacetoxyborohydride (98 mg) were then added and the mixture stirred for 4 hours. Water (10 mL) was then added and the mixture extracted with dichloromethane (30 mL). The organics were combined and evaporated under reduced pressure. The residue was purified by HPLC to give the title compound as a solid (70 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08012979B2 |
| Source dataset | uspto-grants-2011_09 |
| ORD ID | ord-eba2a6c0beec4372a732b981ed47cdb6 |
| Source note | uspto-grants-2011_09 |