Potassium → 4-Cyano-N-(2-(4,4-dimethylcyclohex-1-en-1-yl)-6-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxamide

HRID 456007Notes

Reaction equation

HRID 456007 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:7][CH2:6][C:5]([C:8]2[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([CH:15]3[CH2:20][C:19]([CH3:22])([CH3:21])[O:18][C:17]([CH3:24])([CH3:23])[CH2:16]3)[N:9]=2)=[CH:4][CH2:3]1.[C:26]([C:28]1[N:29]=[C:30]([C:41](O)=[O:42])[N:31]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[CH:32]=1)#[N:27].[K]>>[CH3:1][C:2]1([CH3:25])[CH2:7][CH2:6][C:5]([C:8]2[C:13]([NH:14][C:41]([C:30]3[N:31]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[CH:32]=[C:28]([C:26]#[N:27])[N:29]=3)=[O:42])=[CH:12][CH:11]=[C:10]([CH:15]3[CH2:16][C:17]([CH3:24])([CH3:23])[O:18][C:19]([CH3:22])([CH3:21])[CH2:20]3)[N:9]=2)=[CH:4][CH2:3]1

Participants

4

Reactant 3

HCID 5462222PotassiumHCID 576665392-(4,4-Dimethylcyclohex-1-en-1-yl)-6-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)pyridin-3-amineHCID 591285854-Cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylic acid

Product 1

HCID 576665694-Cyano-N-(2-(4,4-dimethylcyclohex-1-en-1-yl)-6-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxamideYield 92%

Procedure

2-(4,4-Dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-ylamine (as prepared in the previous step, 10.0 g, 0.029 mol) was coupled to 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid, potassium salt as described in Example 1, step (b) to obtain the title compound (15.8 g, 92%) after purification on silica gel (30-70% EtOAc-hexane) as a white solid: Mass spectrum (ESI, m/z): Calcd. for C33H49N5O3Si, 592.3 (M+H), found 592.4.

Sources & evidence

ORD record
ord-acfda929054e4c278da51903dab275f1
Source dataset
uspto-grants-2013_07
Patent number
US08497376B2

Reaction notes

Loading…