Hydrogen Peroxide → HCID 11515891, compound

HRID 1786447Notes

Reaction equation

HRID 1786447 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 rt H2O2 (82.0 μL; 30 wt. % in water). The reaction solution was stirred for 48 h at rt, and water (10.0 mL) was added. The solution was brought to pH=12 using NaOH (25% in water) and extracted with CH2Cl2 (250 mL, 2×50.0 mL). The combined organic layers were washed with water (3×20.0 mL) and were dried over MgSO4. The solvent was removed in vacuo, and the residue was purified by flash chromatography on silica gel (CHCl3/2 M NH3 in MeOH) to give the title compound (121 mg). M calc=353; M+H found=354; 1H NMR (400 MHz, CD3OD): δ7.91-7.87 (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 XXV). 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 CH2Cl2 (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 MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by flash chromatography on silica gel (CHCl3/2 M NH3 in MeOH)

Sources & evidence

ORD record
ord-a571ddaab69d4c9f82dbb29e0efdbdb4
Source dataset
uspto-grants-2009_03
Patent number
US07507756B2

Reaction notes

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