Ethyl Acetate → HCID 178424523, compound

HRID 1190098Notes

Reaction equation

HRID 1190098 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[N:16](COCC[Si](C)(C)C)[CH:17]=[C:18]([C:20]#[N:21])[N:19]=2)=[O:14])=[C:8]([C:30]2[CH2:35][CH2:34][C:33]([CH3:37])([CH3:36])[CH2:32][CH:31]=2)[CH:7]=1)(=[O:3])[NH2:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>C1COCC1>[C:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[NH:16][CH:17]=[C:18]([C:20]#[N:21])[N:19]=2)=[O:14])=[C:8]([C:30]2[CH2:35][CH2:34][C:33]([CH3:37])([CH3:36])[CH2:32][CH:31]=2)[CH:7]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 58994394HCID 58994394, compound

Product 1

HCID 178424523HCID 178424523, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-carbamoyl-ethyl)-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in the previous step, 160 mg, 0.307 mmol) and tetrabutylammonium fluoride (357 μL, 0.357 mmol, 1.0 M in THF) in 4.5 mL of THF was stirred at reflux for 1.5 h under Ar. After cooling to RT, the mixture was treated with EtOAc (40 mL), washed with saturated aq NaHCO3 (5 mL), brine (10 mL) and dried (Na2SO4). The organic layer was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (5% MeOH/DCM) to give 29.2 mg (24%) of the title compound as a white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.09 (d, 1H, J=8.3 Hz), 7.98 (s, 1H), 7.14 (dd, 1H, J=8.3, 2.1 Hz), 7.07 (d, 1H, J=2.1 Hz), 5.71 (m, 1H), 2.89 (t, 2H, J=7.7 Hz), 2.50 (t, 2H, J=7.7 Hz), 2.29 (m, 2H), 2.06 (m, 2H), 1.57 (t, 2H, J=6.3 Hz), 1.07 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C22H25N5O2, 392.2 (M+H). found 392.2.

Workup

  1. temperatureat reflux for 1.5 h under Ar
  2. washwashed with saturated aq NaHCO3 (5 mL), brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe residue was purified by flash chromatography on silica gel (5% MeOH/DCM)

Sources & evidence

ORD record
ord-02e8c937b26d4bdcaafecd969d589bfe
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

Loading…