Ethanol → 4-Cyano-1H-imidazole-2-carboxylic acid [4-bromo-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[N:12](COCC[Si](C)(C)C)[CH:13]=[C:14]([C:16]#[N:17])[N:15]=2)=[O:10])=[C:4]([C:26]2[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[CH2:28][CH:27]=2)[CH:3]=1.CCO.C(O)(C(F)(F)F)=O.C(O)CC>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[NH:12][CH:13]=[C:14]([C:16]#[N:17])[N:15]=2)=[O:10])=[C:4]([C:26]2[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[CH2:28][CH:27]=2)[CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid[4-bromo-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in the previous step, 350 mg, 0.661 mmol) in 5 mL of DCM (CH2Cl2) was added 0.15 mL of EtOH followed by 2.5 mL of TFA. After stirring at RT for 3 h, the mixture was treated with 10 mL of n-propanol and concentrated in vacuo. The residue was triturated with DCM to afford 253 mg (96%) of the title compound as a white solid. 1H-NMR (DMSO-d6; 400 MHz): δ 14.3 (s, 1H), 9.78 (s, 1H), 8.31 (s, 1H), 7.95 (d, 2H, J=8.6 Hz), 7.50 (dd, 2H, J=8.6, 2.3 Hz), 7.41 (d, 1H, J=2.3 Hz), 5.71 (m, 1H), 2.24 (m, 2H), 1.95 (m, 2H), 1.47 (m, 2H), 0.98 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C19H19BrN4O, 399.1 (M+H), found 399.1.
Workup
- concentrationconcentrated in vacuo
- customThe residue was triturated with DCM
Sources & evidence
- ORD record
- ord-9df3be04e1cd4f6799cd0e8218a4f89f
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08497376B2
Reaction notes
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