Nitrogen → 5-(4'-Cyanobenzyl)-1-[2-(cyclohexylthio)pyrid-5-ylmethyl]imidazole

HRID 365470Notes

Reaction equation

[C:1]([C:3]1[CH:22]=[CH:21][C:6]([CH2:7][C:8]2[N:12]([CH2:13][C:14]3[CH:15]=[CH:16][C:17](Br)=[N:18][CH:19]=3)[CH:11]=[N:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2].[CH:23]1([SH:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[H-].[Na+].N#N>CN(C=O)C>[C:1]([C:3]1[CH:22]=[CH:21][C:6]([CH2:7][C:8]2[N:12]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([S:29][CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[N:18][CH:19]=3)[CH:11]=[N:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 110 °C

Procedure

The compound from Example 1, Step 3 (0.16 g 0.45 mmol), cyclohexyl mercaptan (0.16 g, 1.35. mmol) and sodium hydride (60% dispersion in oil, 4.0 equiv, 0.032 g) were suspended in DMF (0.5 mL) in an N2 purged sealed tube and heated at 110° C. for 4hr. The residue was dissolved in methanol and purified on a C18 preperative hplc column. Lyophilized from dioxane/HCl to provide the title compound. FAB-MS: calc: 389 found: 389. 1H-NMR (CD3OD): 1.4-2.1 ppm (10H); 3.8 ppm (1H); 4.2 ppm (2H); 5.45 ppm (2H); 7.2-7.6 ppm (7H); 8.2 ppm (1H); 9.1 ppm (1H).

Workup

custompurged
customsealed tube
dissolutionThe residue was dissolved in methanol
custompurified on a C18 preperative hplc column

Sources & evidence

ORD record: ord-4a30ec68376842108c952348aee48279
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127390

Reaction notes

Loading…