Ethanol → HCID 178466757, compound

HRID 1190203Notes

Reaction equation

HRID 1190203 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[N:14](COCC[Si](C)(C)C)[CH:15]=[C:16]([C:18]#[N:19])[N:17]=2)=[O:12])=[C:6]([C:28]2[CH2:33][CH2:32][C:31]([CH3:35])([CH3:34])[CH2:30][CH:29]=2)[CH:5]=1)(=[O:3])[CH3:2].CCO.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[NH:14][CH:15]=[C:16]([C:18]#[N:19])[N:17]=2)=[O:12])=[C:6]([C:28]2[CH2:33][CH2:32][C:31]([CH3:35])([CH3:34])[CH2:30][CH:29]=2)[CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 6422Trifluoroacetic acidHCID 58994564HCID 58994564, compound

Product 1

HCID 178466757HCID 178466757, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-acetyl-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (8.2 g, 0.016 mol, as prepared in the previous step) in 50 mL of DCM was treated with 6 mL of EtOH followed by 42 mL of TFA. The reaction was stirred for 1 h 45 min, at which time it was diluted with MeOH (100 mL), concentrated to half of the volume and diluted with diethyl ether (80 mL). The result was concentrated in vacuo and dried under vacuum overnight to afford the title compound as a yellow solid (6.00 g, 100%). Mass spectrum (ESI, m/z): Calcd. for C21H22N4O2, 363.1 (M+H). found 363.1.

Workup

  1. concentrationconcentrated to half of the volume
  2. additiondiluted with diethyl ether (80 mL)
  3. concentrationThe result was concentrated in vacuo
  4. customdried under vacuum overnight

Sources & evidence

ORD record
ord-8d29ec01d66f457e81b504506c882771
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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