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-(1,1-dioxo-1lambda6-[1,2,6]thiadiazinan-4-yl)-phenyl]-amide

HRID 340549Notes

Reaction equation

HRID 340549 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]3[CH2:18][NH:17][S:16](=[O:20])(=[O:19])[NH:15][CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH2:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[C:22]([C:24]1[N:25]=[C:26]([C:37](O)=[O:38])[N:27]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH:28]=1)#[N:23].[K+].C(C1N=C(C([O-])=O)N(COCC[Si](C)(C)C)C=1)#N>>[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]3[CH2:14][NH:15][S:16](=[O:20])(=[O:19])[NH:17][CH2:18]3)[CH:10]=[CH:9][C:8]=2[NH:21][C:37]([C:26]2[N:27]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH:28]=[C:24]([C:22]#[N:23])[N:25]=2)=[O:38])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 3

HCID 591285854-Cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylic acidHCID 597712852-Cyclohex-1-enyl-4-(1,1-dioxo-1lambda6-[1,2,6]thiadiazinan-4-yl)-phenylamineHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 597711354-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(1,1-dioxo-1lambda6-[1,2,6]thiadiazinan-4-yl)-phenyl]-amideYield 25%

Procedure

2-Cyclohex-1-enyl-4-(1,1-dioxo-1λ6-[1,2,6]thiadiazinan-4-yl)-phenylamine (as prepared in the previous step, 30.7 mg, 0.100 mmol) was coupled to 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid, potassium salt (as prepared in Example 1, step (d), 33.6 mg, 0.260 mmol) as described in Example 1, step (1) to obtain the title compound (14 mg, 25%) after purification on silica (20-50% EtOAc-hexane): Mass spectrum (ESI, m/z): Calcd. for C26H36N6O4SSi, 557.2 (M+H). found 556.8.

Sources & evidence

ORD record
ord-38aaf484ba5c4b5f8b78688fb2d65c80
Source dataset
uspto-grants-2014_11
Patent number
US08895584B2

Reaction notes

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