HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-(4-Methoxyphenyl)-6-(4-{1-[(methylamino)methyl]cyclopropyl}phenyl)-7-oxo-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carboxamide → 1-(4-Methoxyphenyl)-6-(4-{1-[(methylamino)methyl]cyclopropyl}phenyl)-7-oxo-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-(4-Methoxyphenyl)-6-(4-{1-[(methylamino)methyl]cyclopropyl}phenyl)-7-oxo-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carboxamide | HCID 44581362 | — |
| Catalyst | Thionyl Chloride | HCID 24386 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-(4-Methoxyphenyl)-6-(4-{1-[(methylamino)methyl]cyclopropyl}phenyl)-7-oxo-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carbonitrile | HCID 44581363 | 76.4% |
Reaction Steps
The product of Example 67 (15 mg) was stirred in DMF (0.5 mL) at RT in a capped vial. Two drops of thionyl chloride was added. The reaction was completed in 10 min. The mixture was purified by RP-prep LC-MS (5–98% CH3CN/H2O in a 10-min run) to give pure 1-(4-methoxyphenyl)-6-(4-{1-[(methylamino)methyl]cyclopropyl}phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carbonitrile (11 mg, yield: 76.2%). LC/MS (ESI+) 428.4 (M+H)+, tR=4.49 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07312214B2 |
| Source dataset | uspto-grants-2007_12 |
| ORD ID | ord-7e610fdf21e84e34ab9504f2fb4f01ef |
| Source note | uspto-grants-2007_12 |