4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (3-cyclohex-1-enyl-4'-methanesulfonylamino-biphenyl-4-yl)-amide → HCID 178504995, compound

HRID 1711251Notes

Reaction equation

HRID 1711251 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([C:31]3[CH:36]=[CH:35][C:34]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])=[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:32]=[CH:33][C:34]([NH:37][S:38]([CH3:41])(=[O:39])=[O:40])=[CH:35][CH:36]=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 587548254-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (3-cyclohex-1-enyl-4'-methanesulfonylamino-biphenyl-4-yl)-amide

Product 1

HCID 178504995HCID 178504995, compoundYield 44%

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-4′-methanesulfonylamino-biphenyl-4-yl)-amide (as prepared in the previous step, 29.5 mg, 0.0498 mmol). Silica gel chromatography (5-10% EtOAc/DCM) afforded the title compound (10.1 mg, 44%) as a white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.29 (d, 1H, J=8.6 Hz), 8.01 (s, 1H), 7.60 (d, 2H, J=8.6 Hz), 7.53 (dd, 1H, J=8.4, 2.0 Hz), 7.42 (d, 1H, J=2.0 Hz), 7.33 (d, 2H, J=8.6 Hz), 5.89 (m, 1H), 2.98 (s, 3H), 2.23-2.38 (m, 4H), 1.77-1.93 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C24H23N5O3S, 462.2 (M+H), found 461.9.

Workup

  1. customThe title compound was prepared by the procedure of Example 11, step (g)
  2. customas prepared in the previous step, 29.5 mg, 0.0498 mmol)

Sources & evidence

ORD record
ord-d5ab6393dcab45788f1d5deea1f83665
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

Loading…