HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-5-(3-methyl-8-(methylamino)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one → (R)-4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-5-(3-methyl-8-(methylamino)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-5-(3-methyl-8-(methylamino)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one | HCID 91826322 | — |
| Reactant | tert-butyl 3-(4-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-6-oxo-5,6-dihydropyrrolo[3,4-c]pyrazol-1(4H)-yl)azetidine-1-carboxylate | HCID 117702723 | — |
| Solvent | Ethanol dichloromethane heptane | HCID 86658618 | — |
| Product | (R)-4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-5-(3-methyl-8-(methylamino)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one | HCID 91826390 | — |
Reaction Steps
The title compound (38 mg, 34% yield) was obtained enantiomerically pure (>99% ee) after chiral preparative chromatography (system: Gilson PLC 2020; column: Chiralpak ID 5 μm, 20×250 mm; mobile phase: heptane/CH2Cl2/EtOH 70:25:5; flow: 10 mL/min; detection UV: 275 nm) of the racemic mixture of 4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-5-(3-methyl-8-(methylamino)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Example 113).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08975417B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-9e9873e1f0174337afa9a419ab189f8b |
| Source note | uspto-grants-2015_03 |