Hydrogen Peroxide → HCID 11515891, compound

HRID 915196Notes

Reaction equation

HRID 915196 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:11]([CH3:22])[C:12]([S:15][CH2:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[N:13][CH:14]=2)=[O:9])=[CH:4][CH:3]=1.[OH:23]O.O.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:11]([CH3:22])[C:12]([S:15]([CH2:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[O:23])=[N:13][CH:14]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 11551796HCID 11551796, compound

Product 1

HCID 11515891HCID 11515891, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of (4-Chloro-phenyl)-[2-(3-dimethylamino-propylsulfanyl)-3-methyl-3H-imidazol-4-yl]-methanone (135 mg) in glacial acetic acid (4.00 mL) was added at room temperature H2O2 (82.0 μL; 30 wt. % in water). The reaction solution was stirred for 48 h at room temperature, and water (10.0 mL) was added. The solution was brought to pH=12 using sodium hydroxide (25% in water) and extracted with dichloromethane (250 mL, 2×50.0 mL). The combined organic layers were washed with water (3×20.0 mL) and were dried over magnesium sulfate. The solvent was removed in vacuo, and the residue was purified by flash chromatography on silica gel (CHCl3/NH3, 2 M in methanol) to give the title compound (121 mg). M calc=353; M+H found=354. 1H NMR (400 MHz, CD3OD): δ 7.91-7.87 (m, 2H), 7.70 (s, 1H), 7.60-7.55 (m, 2H), 4.21 (s, 3H), 3.61-3.48 (m, 2H), 2.54-2.43 (m, 2H), 2.21 (s, 6H), 2.04-1.94 (m, 2H). The compound demonstrated useful biological activity when assessed with a [3H]-N-methylhistamine binding assay (see Table in Example XVI II). Step B: Additional Compounds Prepared Following Scheme XI, and Example XVI, Step A. The following compounds of Formula I were prepared following Scheme XI and Example XVI, Step A; and substituting reagents, and adjusting reaction conditions as needed.

Workup

  1. extractionextracted with dichloromethane (250 mL, 2×50.0 mL)
  2. washThe combined organic layers were washed with water (3×20.0 mL)
  3. dry with materialwere dried over magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by flash chromatography on silica gel (CHCl3/NH3, 2 M in methanol)

Sources & evidence

ORD record
ord-3f4940aeb5c34e1b9414c654eb6102de
Source dataset
uspto-grants-2007_09
Patent number
US07265135B2

Reaction notes

Loading…