4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (3-cyclohex-1-enyl-biphenyl-4-yl)-amide → HCID 178510377, compound

HRID 1711253Notes

Reaction equation

HRID 1711253 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:10]=[CH:11][C:12]=2[NH:13][C:14]([C:16]2[N:17](COCC[Si](C)(C)C)[CH:18]=[C:19]([C:21]#[N:22])[N:20]=2)=[O:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>CCOC(C)=O.C(Cl)Cl>[C:1]1([C:7]2[CH:8]=[C:9]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:10]=[CH:11][C:12]=2[NH:13][C:14]([C:16]2[NH:17][CH:18]=[C:19]([C:21]#[N:22])[N:20]=2)=[O:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

3

Reactant 1

HCID 587548104-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (3-cyclohex-1-enyl-biphenyl-4-yl)-amide

Product 1

HCID 178510377HCID 178510377, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

The title compound was prepared by the procedure of Example 11, step (g) using 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (3-cyclohex-1-enyl-biphenyl-4-yl)-amide (as prepared in the previous step, 16 mg, 0.032 mmol). Silica gel chromatography (2-3% EtOAc/DCM) afforded the title compound (7.1 mg, 60%) as a white solid. 1H-NMR (1:1 CDCl3/CD3OD; 400 MHz): δ 8.36 (d, 1H, J=8.6 Hz), 7.88 (s, 1H), 7.59-7.62 (m, 2H), 7.54 (dd, 1H, J=8.6, 2.3 Hz), 7.42-7.46 (m, 3H), 7.34 (m, 1H), 5.92 (m, 1H), 2.29-2.37 (m, 4H), 1.79-1.94 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C23H20N4O, 369.2 (M+H), found 369.1.

Workup

  1. customThe title compound was prepared by the procedure of Example 11, step (g)
  2. customas prepared in the previous step, 16 mg, 0.032 mmol)

Sources & evidence

ORD record
ord-c2bd494aa6514b99adeef54854072790
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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