Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | HCID 69007915 | HCID 69007915 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178510427 | HCID 178510427 | 95.3% |
Reaction Steps
To a solution of 3-(4-{[4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbonyl]-amino}-3-cyclohex-1-enyl-phenyl)-acrylic acid tert-butyl ester (30 mg, 0.055 mmol)(as prepared in the previous step) in 1.0 mL of DCM was added 0.30 mL of TFA, 0.026 mL of EtOH and stirred at RT for 2 h. The mixture was concentrated and the residue triturated with MeOH to give 19 mg (95%) of the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6): δ 14.39 (br s, 1H), 9.83 (s, 1H), 8.38 (d, J=2.5 Hz, 1H), 8.15 (d, J=8.5 Hz, 1H), 7.65 (dd, J=8.5, 1.9 Hz, 1H), 7.57 (d, J=1.9 Hz, 1H), 7.56 (d, J=16.0 Hz, 1H), 6.53 (d, J=16.0 Hz, 1H), 5.83 (m, 1H), 2.31-2.14 (m, 4H), 1.81-1.65 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C20H18N4O3, 363.1 (M+H). found 363.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09221797B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-2825c1c0b19045099d2fd49cad1597bd |
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| Source note | uspto-grants-2015_12 |
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