4-Amino-3-(4,4-dimethyl-cyclohex-1-enyl)-benzamide → 4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-carbamoyl-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide

HRID 1711247Notes

Reaction equation

HRID 1711247 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[C:11]1[CH2:16][CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][CH:12]=1.[K+].[C:20]([C:22]1[N:23]=[C:24]([C:35]([O-])=[O:36])[N:25]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH:26]=1)#[N:21]>CO.C(Cl)Cl>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([NH:1][C:35]([C:24]2[N:25]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH:26]=[C:22]([C:20]#[N:21])[N:23]=2)=[O:36])=[C:3]([C:11]2[CH2:16][CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][CH:12]=2)[CH:4]=1)(=[O:7])[NH2:8]

Participants

4

Reactant 2

HCID 587548584-Amino-3-(4,4-dimethyl-cyclohex-1-enyl)-benzamideHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 587548654-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-carbamoyl-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amideYield 94%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared by the procedure of Example 11, step (f) using 4-amino-3-(4,4-dimethyl-cyclohex-1-enyl)-benzamide (as prepared in the previous step, 51.0 mg, 0.209 mmol) and potassium 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate (as prepared in Example 11, step (d), 70.2 mg, 0.230 mmol). Silica gel chromatography (0-2% MeOH/DCM) afforded the title compound (91 mg, 94%) as a white solid. Mass spectrum (ESI, m/z): Calcd. for C26H35N5O3Si, 494.3 (M+H), found 494.1.

Workup

  1. customThe title compound was prepared by the procedure of Example 11, step (f)

Sources & evidence

ORD record
ord-d7d1dae2e12f451ea6ec45de10265be8
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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