4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4-acetyl-2-cyclohex-1-enyl-phenyl)-amide → HCID 178466756, compound

HRID 1711241Notes

Reaction equation

HRID 1711241 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][CH2:31][CH2:30][CH:29]=2)[CH:5]=1)(=[O:3])[CH3:2]>CCOC(C)=O.C(Cl)Cl>[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][CH2:31][CH2:30][CH:29]=2)[CH:5]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 594575354-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4-acetyl-2-cyclohex-1-enyl-phenyl)-amide

Product 1

HCID 178466756HCID 178466756, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

The title compound was prepared by the procedure of Example 15, step (c) using 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, 40.0 mg, 0.0862 mmol). Silica gel chromatography (10% EtOAc/DCM) afforded the title compound (26.2 mg, 91%) as a white solid. 1H-NMR (CDCl3; 400 MHz): δ 11.59 (s, 1H), 9.79 (s, 1H), 8.50 (d, 1H, J=8.6 Hz), 7.92 (dd, 1H, J=8.6, 2.0 Hz), 7.82 (d, 1H, J=2.0 Hz), 7.78 (s, 1H), 5.92 (m, 1H), 2.62 (s, 3H), 2.23-2.39 (m, 4H), 1.77-1.94 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C19H18N4O2, 335.1 (M+H), found 335.1.

Workup

  1. customThe title compound was prepared by the procedure of Example 15, step (c)
  2. customas prepared in the previous step, 40.0 mg, 0.0862 mmol)

Sources & evidence

ORD record
ord-dceb2b70b1344db0a5d882ccbbf73dbe
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

Loading…