p-Toluenesulfonic acid → 4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-methyl-[1,3]dioxan-2-yl)-phenyl]-amide

HRID 1023657Notes

Reaction equation

HRID 1023657 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3([CH3:18])[O:17][CH2:16][CH2:15][O:14]3)[CH:10]=[CH:9][C:8]=2[NH:19][C:20]([C:22]2[N:23]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH:24]=[C:25]([C:27]#[N:28])[N:26]=2)=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH2:37](O)CCO.CC1C=CC(S(O)(=O)=O)=CC=1>>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3([CH3:18])[O:17][CH2:16][CH2:37][CH2:15][O:14]3)[CH:10]=[CH:9][C:8]=2[NH:19][C:20]([C:22]2[N:23]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:35])([CH3:36])[CH3:34])[CH:24]=[C:25]([C:27]#[N:28])[N:26]=2)=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 589950804-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-methyl-[1,3]dioxolan-2-yl)-phenyl]-amide

Product 1

HCID 711626534-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-methyl-[1,3]dioxan-2-yl)-phenyl]-amide

Procedure

The title compound was prepared from 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4-acetyl-2-cyclohex-1-enyl-phenyl)-amide (as prepared in Example 1, step (h), 0.58 mmol), 1,3-propanediol (882 mg, 11.6 mmol) and catalytic PTSA according to the procedure in Example 1, step (h) (147 mg, 49%). Mass spectrum (ESI, m/z): Calcd. for C28H38N4O4Si, 523.2 (M+H), found 523.3.

Sources & evidence

ORD record
ord-4418092463e34f5797393a93f364e357
Source dataset
uspto-grants-2014_05
Patent number
US08722718B2

Reaction notes

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