p-Toluenesulfonic acid → 4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-methyl-[1,3]dioxolan-2-yl)-phenyl]-amide

HRID 1777318Notes

Reaction equation

HRID 1777318 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[N:14]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:15]=[C:16]([C:18]#[N:19])[N:17]=2)=[O:12])=[C:6]([C:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]=2)[CH:5]=1)(=[O:3])[CH3:2].[CH:34](O)([OH:36])[CH3:35].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.CCOC(C)=O>[C:28]1([C:6]2[CH:5]=[C:4]([C:1]3([CH3:2])[O:36][CH2:34][CH2:35][O:3]3)[CH:9]=[CH:8][C:7]=2[NH:10][C:11]([C:13]2[N:14]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:26])([CH3:27])[CH3:25])[CH:15]=[C:16]([C:18]#[N:19])[N:17]=2)=[O:12])[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 1512111,1-EthanediolHCID 594575354-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4-acetyl-2-cyclohex-1-enyl-phenyl)-amide

Product 1

HCID 589950804-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-methyl-[1,3]dioxolan-2-yl)-phenyl]-amideYield 68%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4-acetyl-2-cyclohex-1-enyl-phenyl)-amide (as prepared in the previous step, 135 mg, 0.290 mmol), ethanediol (363 mg, 5.80 mmol) and catalytic p-toluenesulfonic acid (PTSA) in 21 mL of benzene were heated at reflux under Dean-Stark conditions for 4 h. The reaction was diluted with EtOAc (25 mL), washed with water (3×20 mL), dried (Na2SO4), and concentrated in vacuo. Purification of the residue using preparative TLC (10% MeOH—CHCl3) afforded 100 mg (68%) of the title compound as a white solid. Mass spectrum (ESI, m/z): Calcd. for C27H36N4O4Si, 509.2 (M+H). found 509.0.

Workup

  1. temperaturewere heated
  2. temperatureat reflux under Dean-Stark conditions for 4 h
  3. washwashed with water (3×20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue

Sources & evidence

ORD record
ord-5e65440b2fa549c284037666ebf924b7
Source dataset
uspto-grants-2016_02
Patent number
US09266866B2

Reaction notes

Loading…