Nitrogen → 5-(4'-Cyanobenzyl)-1-[2-(3"methylphenylthio)pyrid-5-ylmethyl)imidazole

HRID 365468Notes

Reaction equation

HRID 365468 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].[CH3:23][C:24]1[CH:25]=[C:26]([SH:30])[CH:27]=[CH:28][CH:29]=1.C(N(CC)CC)C.N#N>>[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:30][C:26]4[CH:27]=[CH:28][CH:29]=[C:24]([CH3:23])[CH:25]=4)=[N:18][CH:19]=3)[CH:11]=[N:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 4

HCID 947NitrogenHCID 79303-ThiocresolHCID 8471TriethylamineHCID 232920655-(4-Cyanobenzyl)-1-(2-bromopyrid-5-ylmethyl)imidazole

Product 1

HCID 98437055-(4'-Cyanobenzyl)-1-[2-(3"methylphenylthio)pyrid-5-ylmethyl)imidazole

Conditions

Temperature
105 °C

Procedure

The compound from Step 3 (0.28 mmol, 0.164 g), 3-methyl thiophenol (0.85 mmol, 0.106 g) and triethylamine (3.59 mmol, 0.36 g) were placed in an N2 purged sealed tube. This was heated at 105° C. for 15 hr. 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: 396.4 found: 397.2 1H-NMR (CD3OD): 2.4 ppm (s, 3H); 4.2 ppm (s, 2H); 5.4 ppm (s, 2H); 7.2-7.6 ppm (1OH); 8.1 ppm (s, 1H); 9.1 ppm (s, 1H).

Workup

  1. custompurged
  2. customsealed tube
  3. dissolutionThe residue was dissolved in methanol
  4. custompurified on a C18 preperative hplc column

Sources & evidence

ORD record
ord-13f1214b5ecb44e9ba604c4065a2119f
Source dataset
uspto-grants-2000_10
Patent number
US06127390

Reaction notes

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