Ethyl Acetate → HCID 24759505, compound

HRID 1711239Notes

Reaction equation

HRID 1711239 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)[C:13]([C:18]([OH:21])([CH3:20])[CH3:19])=[C:14]([C:16]#[N:17])[N:15]=2)=[O:10])=[C:4]([C:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=2)[CH:3]=1.[F-].CCOC(C)=O>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[NH:12][C:13]([C:18]([OH:21])([CH3:20])[CH3:19])=[C:14]([C:16]#[N:17])[N:15]=2)=[O:10])=[C:4]([C:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 28179Fluoride IonHCID 58754814HCID 58754814, compound

Product 1

HCID 24759505HCID 24759505, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-cyano-5-(1-hydroxy-1-methyl-ethyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4-bromo-2-cyclohex-1-enyl-phenyl)-amide (as prepared in the previous step, 40.0 mg, 0.0715 mmol) and tetrabutylammomium fluoride (357 μL, 0.357 mmol, 1.0 M in THF) in 2.0 mL of THF was stirred under Ar at 50° C. for 16 h and at reflux for 3 h. After cooling to RT, the mixture was treated with EtOAc (40 mL) and washed with saturated NH4Cl aqueous solution (5 mL), brine (10 mL) and dried (Na2SO4). The organic layer was concentrated in vacuo and residue was purified by flash chromatography on silica gel (5-10% EtOAc/DCM) to give 26 mg (84%) of the title compound as a white solid. 1H-NMR (CDCl3; 400 MHz): δ 11.79 (s, 1H), 9.55 (s, 1H), 8.23 (d, 1H, J=8.6 Hz), 7.42 (dd, 1H, J=8.6, 2.3 Hz), 7.33 (d, 1H, J=2.3 Hz), 5.87 (m, 1H), 5.08 (s, 1H), 2.16-2.34 (m, 4H), 1.83 (s, 6H), 1.71-1.88 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C20H21BrN4O2, 429.1 (M+H), found 428.9.

Workup

  1. temperatureat reflux for 3 h
  2. temperatureAfter cooling to RT
  3. washwashed with saturated NH4Cl aqueous solution (5 mL), brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationThe organic layer was concentrated in vacuo and residue
  6. customwas purified by flash chromatography on silica gel (5-10% EtOAc/DCM)

Sources & evidence

ORD record
ord-f188e132f26f49d492b3940106802eae
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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