Carbamate → [5-(3,5-dichlorophenyl)sulfanyl-4-isopropyl-1-(4-pyridylmethyl)imidazol-2-yl]methyl N-acetylcarbamate

HRID 1005552

Reaction equation

HRID 1005552 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:13]([CH2:22][OH:23])=[N:12][C:11]=2[CH:24]([CH3:26])[CH3:25])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])N.[C:31]([N:34]=[C:35]=[O:36])(=[O:33])[CH3:32]>>[C:31]([NH:34][C:35](=[O:36])[O:23][CH2:22][C:13]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:11]([CH:24]([CH3:26])[CH3:25])[N:12]=1)(=[O:33])[CH3:32]

Participants

4

Reactant 3

HCID 276CarbamateHCID 9844329{5-[(3,5-Dichlorophenyl)sulfanyl]-4-isopropyl-1-((pyridin-4-YL)methyl)imidazol-2-YL}methanolHCID 12300404Acetyl isocyanate

Product 1

HCID 478192[5-(3,5-dichlorophenyl)sulfanyl-4-isopropyl-1-(4-pyridylmethyl)imidazol-2-yl]methyl N-acetylcarbamateYield 76%

Procedure

5-(3,5-Dichlorophenylthio)-4-isoproyl-1-(4-pyridylmethyl)-2-hydroxymethyl-1H-imidazole (89) (245 mg, 0.6 mmol) prepared in accordance with the method as described in WO 96/10019 was converted to the carbamate with acetyl isocyanate (5 eq.) in the same manner as the example 66 to give the compound 90 (225 mg, 76%) as crystals. Mp. 135-137° C. Rf 0.32 (10:1 EtOAc - CH3OH).

Sources & evidence

ORD record
ord-06b7f5f2e4d54f3ab5491022a5be57ec
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Linked notes

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