Water → HCID 178504697, compound

HRID 2231114Notes

Reaction equation

HRID 2231114 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([SH:23])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.Cl.Cl[CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1.C(N(CC)CC)C.O>CC(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([S:23][CH2:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 178504698HCID 178504698, compound

Product 1

HCID 178504697HCID 178504697, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-(4-fluorophenyl)-5-(4-(methylsulfonyl)phenyl]-1H-imidazole-2-thiol (Example 49) (100 mg, 0.29 mmol), 2-chloromethylquinoline hydrochloride (62 mg, 0.29 mmol) and triethylamine (60 mg, 0.58 mmol) in 2-propanol (5 ml) was heated at reflux under an argon atmosphere for 4 hours. The reaction was cooled, poured into water (25 ml) and extracted with ethyl acetate. After drying over sodium sulfate, the solvent was removed and the residue was purified by chromatography on silica gel using 50% ethyl acetate in toluene as the eluent to give 136 mg (85%) of the desired product. Although initially an oil, this material crystallized on standing: mp 179-182° C. Anal. Calc'd. for C26H20N3O2FS2.5H2O (MW 498.60): C, 62.63; H, 4.25; N, 8.43; S, 12.86. Found: C, 62.98; H, 4.43; N, 8.03; S, 12.60.

Workup

  1. temperatureat reflux under an argon atmosphere for 4 hours
  2. temperatureThe reaction was cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialAfter drying over sodium sulfate
  5. customthe solvent was removed
  6. customthe residue was purified by chromatography on silica gel using 50% ethyl acetate in toluene as the eluent

Sources & evidence

ORD record
ord-e381a479f0f648768ecd9b2a98928430
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

Loading…