4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [5-acetyl-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide → HCID 178466077, compound

HRID 1711257Notes

Reaction equation

HRID 1711257 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:28]2[CH2:33][CH2:32][C:31]([CH3:35])([CH3:34])[CH2:30][CH:29]=2)=[C:8]([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])[CH:9]=1)(=[O:3])[CH3:2]>CCOC(C)=O.C(Cl)Cl>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:28]2[CH2:33][CH2:32][C:31]([CH3:35])([CH3:34])[CH2:30][CH:29]=2)=[C:8]([NH:10][C:11]([C:13]2[NH:14][CH:15]=[C:16]([C:18]#[N:19])[N:17]=2)=[O:12])[CH:9]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 587548694-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [5-acetyl-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide

Product 1

HCID 178466077HCID 178466077, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

The title compound was prepared by the procedure of Example 11, step (g) using 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [5-acetyl-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in the previous step, 200 mg, 0.406 mmol). Silica gel chromatography (5-15% EtOAc/DCM) afforded the title compound (134 mg, 91%) as a white solid. 1H-NMR (CDCl3; 400 MHz): δ 12.85 (s, 1H), 9.75 (s, 1H), 9.13 (d, 1H, J=1.8 Hz), 8.18 (d, 1H, J=2.5 Hz), 7.75 (dd, 1H, J=8.1, 1.8 Hz), 7.32 (d, 1H, J=8.1 Hz), 5.86 (m, 1H), 2.67 (s, 3H), 2.28-2.35 (m, 2H), 2.08-2.19 (m, 2H), 1.62 (t, 2H, J=6.3 Hz), 1.13 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C21H22N4O2, 363.2 (M+H), found 363.2.

Workup

  1. customThe title compound was prepared by the procedure of Example 11, step (g)
  2. customas prepared in the previous step, 200 mg, 0.406 mmol)

Sources & evidence

ORD record
ord-72e0054cdbfc4d8e97e97c55b797c846
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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