4-Cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylic acid → 4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-oxo-hexahydro-pyrimidin-5-yl)-phenyl]-amide

HRID 408912Notes

Reaction equation

HRID 408912 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][NH:12][C:11](=[O:14])[NH:10][CH2:9]2)=[CH:4][C:3]=1[C:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=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+].C(C1N=C(C([O-])=O)N(COCC[Si](C)(C)C)C=1)#N>>[C:15]1([C:3]2[CH:4]=[C:5]([CH:8]3[CH2:9][NH:10][C:11](=[O:14])[NH:12][CH2:13]3)[CH:6]=[CH:7][C:2]=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])[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=1

Participants

4

Reactant 3

HCID 591285854-Cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylic acidHCID 597712825-(4-Amino-3-cyclohex-1-enyl-phenyl)-tetrahydro-pyrimidin-2-oneHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 597711634-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-oxo-hexahydro-pyrimidin-5-yl)-phenyl]-amide

Procedure

5-(4-Amino-3-cyclohex-1-enyl-phenyl)-tetrahydro-pyrimidin-2-one (22 mg, as prepared in the previous step) was coupled to 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid, potassium salt (as prepared in Example 1, step (d), 27.2 mg, 0.0890 mmol) as described in Example 1, step (l) to obtain the title compound (14 mg, over two steps) after purification on silica (3% MeOH-EtOAc): Mass spectrum (ESI, m/z): Calcd. for C27H36N6O3Si, 521.2 (M+H). found 521.1.

Sources & evidence

ORD record
ord-dbe839b1160d47b0983d6967da6e27d7
Source dataset
uspto-grants-2014_06
Patent number
US08759347B2

Reaction notes

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