Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydroxylamine | HCID 787 | — |
| Reactant | HCID 44447253 | HCID 44447253 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 178513319 | HCID 178513319 | 23% |
Reaction Steps
To a solution of 5-cyano-furan-2-carboxylic acid (2,4-di-piperidin-1-yl-phenyl)-amide (48 mg, 0.12 mmol, as prepared in the previous step) in 1 mL of EtOH at room temperature was added NH2OH (26 mg, 0.4 mmol, 50% wt/H2O) via syringe. The reaction was heated to reflux for 10 min, and then cooled to 0° C. The bright yellow precipitate was filtered, washed with cold 50% EtOH—H2O (2 mL) and dried to afford 11 mg (23%) of the title compound as a bright yellow solid. 1H-NMR (DMSO-d6; 400 MHz): δ 9.83 (s, 1H), 9.37 (s, 1H), 7.84 (d, 1H, J=9.0 Hz), 7.21 (d, 1H, J=3.5 Hz), 6.89 (d, 1H, J=3.6 Hz), 6.74 (s, 1H), 6.66 (d, 1H, J=8.8 Hz), 5.96 (br s, 2H), 3.08-3.10 (m, 4H), 2.78-2.77 (m, 4H), 1.71-1.52 (m, 12H); Mass spectrum (ESI, m/z): Calcd. for C22H29N5O3 412.2 (M+H), found 412.2;
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07705042B2 |
|---|
| Source dataset | uspto-grants-2010_04 |
|---|
| ORD ID | ord-f3bfe403a92c4947a127fb7fc95779e2 |
|---|
| Source note | uspto-grants-2010_04 |
|---|