Water → HCID 53681965, compound

HRID 1416043Notes

Reaction equation

HRID 1416043 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:11]([S:12][C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=3)=[C:10]([CH:21]([CH3:23])[CH3:22])[N:9]=[C:8]2[CH2:24][OH:25])=[CH:4][CH:3]=1.CN([C:31]1[CH:36]=CC=CN=1)C.[C:37](OC(=O)C)(=[O:39])[CH3:38].[OH2:44]>C(Cl)Cl>[C:37]([O:25][CH2:24][C:8]1[N:7]([CH2:6][C:5]2[CH:26]=[CH:27][C:2]([NH:1][C:36](=[O:44])[CH3:31])=[CH:3][CH:4]=2)[C:11]([S:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)=[C:10]([CH:21]([CH3:23])[CH3:22])[N:9]=1)(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 4740301H-Imidazole-2-methanol, 1-((4-aminophenyl)methyl)-5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-

Product 1

HCID 53681965HCID 53681965, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In methylene chloride was dissolved 200 mg of 1-(p-aminobenzyl)-5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1H-imidazole (104a), there were added 116 mg of dimethylaminopyridine and 212 μl of acetic anhydride under ice-cooling, and the mixture was allowed to warm up to room temperature and stirred for 1 hour. After completion of the reaction, the mixture was diluted with water, extracted with methylene chloride, the extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (methylene chloride:ethyl acetate=2:1)to provide 2-acetoxymethyl-1-(p-N-acetylaminobenzyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole. The compound was dissolved in 10 ml of methanol, and under ice-cooling, 1 ml of 1M sodium methoxide solution was added. The mixture was allowed to warm up to room temperature and stirred for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, and 41.2 mg of Compound I-117 was obtained (yield 19%).

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. extractionextracted with methylene chloride
  4. dry with materialthe extract was dried over sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel chromatography (methylene chloride

Sources & evidence

ORD record
ord-1a1228e7ae26405c8d405b2d327c58e1
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

Loading…