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

HRID 1711244Notes

Reaction equation

HRID 1711244 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][CH2:14][CH2:13][CH:12]=1.[K+].[C:18]([C:20]1[N:21]=[C:22]([C:33]([O-])=[O:34])[N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=1)#[N:19]>CO.C(Cl)Cl>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([NH:1][C:33]([C:22]2[N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=[C:20]([C:18]#[N:19])[N:21]=2)=[O:34])=[C:3]([C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=2)[CH:4]=1)(=[O:7])[NH2:8]

Participants

4

Reactant 2

HCID 587548054-Amino-3-cyclohex-1-enyl-benzamideHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 587548354-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4-carbamoyl-2-cyclohex-1-enyl-phenyl)-amideYield 98%

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-cyclohex-1-enyl-benzamide (as prepared in the previous step, 100 mg, 0.462 mmol) and potassium 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate (as prepared in Example 11, step (d), 155 mg, 0.509 mmol). Silica gel chromatography (1-2% MeOH/DCM) afforded the title compound (210 mg, 98%) as a white solid. Mass spectrum (ESI, m/z): Calcd. for C24H31N5O3Si, 466.2 (M+H), found 466.1.

Workup

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

Sources & evidence

ORD record
ord-bd7d0ef1e16643b889cf8063f0233edf
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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