HCID 58994512, compound → HCID 58994394, compound

HRID 1190097Notes

Reaction equation

HRID 1190097 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH2:12])=[O:11])=[CH:4][C:3]=1[C:13]1[CH2:18][CH2:17][C:16]([CH3:20])([CH3:19])[CH2:15][CH:14]=1.[C:21]([C:23]1[N:24]=[C:25]([C:36]([O-])=[O:37])[N:26]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:27]=1)#[N:22].[K+]>CO.C(Cl)Cl>[C:10]([CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:36]([C:25]2[N:26]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:27]=[C:23]([C:21]#[N:22])[N:24]=2)=[O:37])=[C:3]([C:13]2[CH2:18][CH2:17][C:16]([CH3:20])([CH3:19])[CH2:15][CH:14]=2)[CH:4]=1)(=[O:11])[NH2:12]

Participants

4

Reactant 2

HCID 58994512HCID 58994512, compoundHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 58994394HCID 58994394, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared by the coupling procedure of Example 7, step (e) using 3-[4-amino-3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-propionamide (as prepared in the previous step, 75.0 mg, 0.307 mmol), and potassium 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate (as prepared in Example 1, step (d), 103 mg, 0.338 mmol). Silica gel chromatography (0-2% MeOH/DCM) afforded the title compound (124 mg, 82%) as a white solid. Mass spectrum (ESI, m/z): Calcd. for C28H39N5O3Si, 522.3 (M+H). found 522.1.

Workup

  1. customThe title compound was prepared by the coupling procedure of Example 7, step (e)

Sources & evidence

ORD record
ord-55d6084cb27f4f77b32df40322bd07c6
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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