HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → HCID 67085298, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 1H-Indazole-5-carboxaldehyde | HCID 21250644 | — |
| Reactant | 3-Amino-4,4,4-trifluorobut-2-enenitrile | HCID 53401096 | — |
| Reactant | Sodium 1-cyanoprop-1-en-2-olate | HCID 74083625 | — |
| Solvent | 1-Pentanol | HCID 6276 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67085298 | HCID 67085298 | — |
Reaction Steps
A mixture of 250 mg (1.71 mmol) 1H-indazole-5-carbaldehyde, 180 mg (1.71 mmol) sodium 1-cyanoprop-1-en-2-olate and 931 mg (6.84 mmol) 3-amino-4,4,4-trifluorobut-2-enenitrile [preparation: A. W. Lutz, U.S. Pat. No. 3,635,977; C. G. Krespan, J. Org. Chem. 34, 42 (1969)] in 1-pentanol (2.5 ml) and acetic acid (0.15 ml) was heated to 105° C. overnight. After cooling, the reaction mixture was diluted with THF and directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient) yielding 131 mg (23% of th.) of the racemic title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09422263B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-a12aa752af594cf4a7d7c35fb3121c5f |
| Source note | uspto-grants-2016_08 |