HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 6-acetyl-4-(2-chlorophenyl)-2,4-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 2-Chlorobenzaldehyde | HCID 6996 | — |
| Reactant | Methyl 2,2-dimethoxypropionate | HCID 82339 | — |
| Reactant | HCID 178418806 | HCID 178418806 | — |
| Reactant | 4-(2-chlorophenyl)-6-(1,1-dimethoxyethyl)-2,4-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile | HCID 178496203 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 6-acetyl-4-(2-chlorophenyl)-2,4-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile | HCID 178466933 | 85.4% |
| Product | 4-(2-chlorophenyl)-6-(1,1-dimethoxyethyl)-2,4-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile | HCID 178496203 | — |
Reaction Steps
4-(2-Chlorophenyl)-5-cyano-4,7-dihydro-6-(1,1-dimethoxyethyl)-2H-pyrazolo[3,4-b]pyridine was prepared from methyl 2,2-dimethoxypropionate, 2-chlorobenzaldehyde and 3-aminopyrazole in the same manner as in Example 1001. To a solution of 4-(2-chlorophenyl)-5-cyano-4,7-dihydro-6-(1,1-dimethoxyethyl)-2H-pyrazolo[3,4-b]pyridine (1.0 g) in dichloromethane (10 mL) was added a trifluoroacetic acid (10 mL) under ice-cooling and the mixture was stirred under ice-cooling for 1 hour. The solvent was evaporated and the obtained residue was crystallized from ethyl acetate to give the title compound (370 mg) as white crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06977262B2 |
| Source dataset | uspto-grants-2005_12 |
| ORD ID | ord-dab1f6acc3a94d9a84440008e651fd88 |
| Source note | uspto-grants-2005_12 |