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 340544Notes

Reaction equation

HRID 340544 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 (1) 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-05a75160fcb043ae95381189b51081c9
Source dataset
uspto-grants-2014_11
Patent number
US08895584B2

Reaction notes

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